JPS6197296A - リン酸誘導体の製造法 - Google Patents

リン酸誘導体の製造法

Info

Publication number: JPS6197296A
Authority: JP; Japan
Prior art keywords: group; reaction; added; act; solution
Prior art date: 1984-10-19
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Granted

Application number

JP59218245A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0582396B2 (de

Inventor

Ryoji Noyori

良治野依

Yoshihiro Hayakawa

芳宏早川

Mamoru Uchiyama

守内山

Tadahito Nobori

忠仁昇

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Seikagaku Corp

Original Assignee

Seikagaku Corp

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1984-10-19

Filing date

1984-10-19

Publication date

1986-05-15

1984-10-19 Application filed by Seikagaku Corp filed Critical Seikagaku Corp

1984-10-19 Priority to JP59218245A priority Critical patent/JPS6197296A/ja

1986-05-15 Publication of JPS6197296A publication Critical patent/JPS6197296A/ja

1993-11-18 Publication of JPH0582396B2 publication Critical patent/JPH0582396B2/ja

Status Granted legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 15
AFINAILKDBCXMX-PBHICJAKSA-N (2s,3r)-2-amino-3-hydroxy-n-(4-octylphenyl)butanamide Chemical compound CCCCCCCCC1=CC=C(NC(=O)[C@@H](N)[C@@H](C)O)C=C1 AFINAILKDBCXMX-PBHICJAKSA-N 0.000 title claims description 5
150000001875 compounds Chemical class 0.000 claims abstract description 39
239000003795 chemical substances by application Substances 0.000 claims abstract description 29
239000002777 nucleoside Substances 0.000 claims abstract description 27
230000000865 phosphorylative effect Effects 0.000 claims abstract description 25
150000003833 nucleoside derivatives Chemical class 0.000 claims abstract description 18
150000004795 grignard reagents Chemical class 0.000 claims abstract description 14
239000007818 Grignard reagent Substances 0.000 claims abstract description 13
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
125000003118 aryl group Chemical group 0.000 claims abstract description 8
150000002148 esters Chemical class 0.000 claims abstract description 8
125000005843 halogen group Chemical group 0.000 claims abstract description 7
229910052736 halogen Inorganic materials 0.000 claims abstract 3
150000002367 halogens Chemical class 0.000 claims abstract 2
-1 magnesium alkoxide Chemical class 0.000 claims description 28
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
239000011777 magnesium Substances 0.000 claims description 17
229910052749 magnesium Inorganic materials 0.000 claims description 17
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000004429 atom Chemical group 0.000 claims description 5
125000004104 aryloxy group Chemical group 0.000 claims description 4
150000003014 phosphoric acid esters Chemical class 0.000 claims description 4
150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 3
NYHBQMYGNKIUIF-UUOKFMHZSA-N Guanosine Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O NYHBQMYGNKIUIF-UUOKFMHZSA-N 0.000 abstract description 5
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239000002342 ribonucleoside Substances 0.000 abstract description 3
150000002894 organic compounds Chemical class 0.000 abstract description 2
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238000006243 chemical reaction Methods 0.000 description 41
239000000243 solution Substances 0.000 description 41
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 37
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239000000203 mixture Substances 0.000 description 28
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238000003756 stirring Methods 0.000 description 20
238000000034 method Methods 0.000 description 19
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238000006366 phosphorylation reaction Methods 0.000 description 8
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FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
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239000002184 metal Substances 0.000 description 6
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238000005119 centrifugation Methods 0.000 description 5
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 5
239000001177 diphosphate Substances 0.000 description 5
XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 5
235000011180 diphosphates Nutrition 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
238000010898 silica gel chromatography Methods 0.000 description 5
229910052717 sulfur Inorganic materials 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
DRTQHJPVMGBUCF-XVFCMESISA-N Uridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-XVFCMESISA-N 0.000 description 4
230000004913 activation Effects 0.000 description 4
125000003277 amino group Chemical group 0.000 description 4
239000000872 buffer Substances 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
238000010828 elution Methods 0.000 description 4
239000007800 oxidant agent Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
229940125782 compound 2 Drugs 0.000 description 3
239000002862 dinucleoside phosphate Substances 0.000 description 3
238000010494 dissociation reaction Methods 0.000 description 3
230000005593 dissociations Effects 0.000 description 3
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 3
125000004433 nitrogen atom Chemical group N* 0.000 description 3
239000002773 nucleotide Substances 0.000 description 3
238000000746 purification Methods 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
230000014616 translation Effects 0.000 description 3
RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 2
UHDGCWIWMRVCDJ-UHFFFAOYSA-N 1-beta-D-Xylofuranosyl-NH-Cytosine Natural products O=C1N=C(N)C=CN1C1C(O)C(O)C(CO)O1 UHDGCWIWMRVCDJ-UHFFFAOYSA-N 0.000 description 2
LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 description 2
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
CGSDOACAGDJPAM-UHFFFAOYSA-N Adenylyl-(5'-2')-5'-adenylsaeure Natural products C1=NC2=C(N)N=CN=C2N1C1OC(COP(O)(O)=O)C(O)C1OP(O)(=O)OCC(C(O)C1O)OC1N1C(N=CN=C2N)=C2N=C1 CGSDOACAGDJPAM-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
UHDGCWIWMRVCDJ-PSQAKQOGSA-N Cytidine Natural products O=C1N=C(N)C=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-PSQAKQOGSA-N 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
102000014150 Interferons Human genes 0.000 description 2
108010050904 Interferons Proteins 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
101100170604 Mus musculus Dmap1 gene Proteins 0.000 description 2
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
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OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
229920001091 Poly(octyl cyanoacrylate) Polymers 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
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238000010586 diagram Methods 0.000 description 2
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DNORZUSMZSZZKU-UHFFFAOYSA-N ethyl 2-[5-(4-chlorophenyl)pentyl]oxirane-2-carboxylate Chemical compound C=1C=C(Cl)C=CC=1CCCCCC1(C(=O)OCC)CO1 DNORZUSMZSZZKU-UHFFFAOYSA-N 0.000 description 2
238000010353 genetic engineering Methods 0.000 description 2
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CQRPUKWAZPZXTO-UHFFFAOYSA-M magnesium;2-methylpropane;chloride Chemical compound [Mg+2].[Cl-].C[C-](C)C CQRPUKWAZPZXTO-UHFFFAOYSA-M 0.000 description 2
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229910001629 magnesium chloride Inorganic materials 0.000 description 1
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239000000463 material Substances 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 1
239000012038 nucleophile Substances 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
150000003017 phosphorus Chemical class 0.000 description 1
108091033319 polynucleotide Proteins 0.000 description 1
102000040430 polynucleotide Human genes 0.000 description 1
239000002157 polynucleotide Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
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GRJJQCWNZGRKAU-UHFFFAOYSA-N pyridin-1-ium;fluoride Chemical compound F.C1=CC=NC=C1 GRJJQCWNZGRKAU-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical class O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
239000003998 snake venom Substances 0.000 description 1
210000004894 snout Anatomy 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000010421 standard material Substances 0.000 description 1
150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
230000006103 sulfonylation Effects 0.000 description 1
238000005694 sulfonylation reaction Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000002480 thymidyl group Chemical group 0.000 description 1
238000013519 translation Methods 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
239000001226 triphosphate Substances 0.000 description 1
229940035893 uracil Drugs 0.000 description 1
125000002223 uridyl group Chemical group 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
230000009385 viral infection Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
229940102001 zinc bromide Drugs 0.000 description 1

Classifications

- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Saccharide Compounds (AREA)

JP59218245A 1984-10-19 1984-10-19 リン酸誘導体の製造法 Granted JPS6197296A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP59218245A JPS6197296A (ja)	1984-10-19	1984-10-19	リン酸誘導体の製造法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP59218245A JPS6197296A (ja)	1984-10-19	1984-10-19	リン酸誘導体の製造法

Publications (2)

Publication Number	Publication Date
JPS6197296A true JPS6197296A (ja)	1986-05-15
JPH0582396B2 JPH0582396B2 (de)	1993-11-18

Family

ID=16716863

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP59218245A Granted JPS6197296A (ja)	1984-10-19	1984-10-19	リン酸誘導体の製造法

Country Status (1)

Country	Link
JP (1)	JPS6197296A (de)

1984
- 1984-10-19 JP JP59218245A patent/JPS6197296A/ja active Granted

Also Published As

Publication number	Publication date
JPH0582396B2 (de)	1993-11-18

Legal Events

Date	Code	Title	Description
2004-10-19	EXPY	Cancellation because of completion of term

Publication	Publication Date	Title
AU710074B2 (en)	1999-09-16	Novel method of preparation of known and novel 2'-modified nucleosides by intramolecular nucleophilic displacement
US5218088A (en)	1993-06-08	Process for preparing dithiophosphate oligonucleotide analogs via nucleoside thiophosphoramidite intermediates
US5359052A (en)	1994-10-25	Chalcophospholanes useful in the synthesis of oligonucleoside phosphorothioates, phosphorodithioates and related selenates
JP2705913B2 (ja)	1998-01-28	インビトロにおけるオリゴヌクレオチド合成法
US4980460A (en)	1990-12-25	Protected nucleosides which permit more efficient oligonucleotide syntheses
CA2386221C (en)	2009-06-30	Compounds for protecting hydroxyls and methods for their use
Murata et al.	1990	Synthesis and characterization of a substrate for T4 endonuclease V containing a phosphorodithioate linkage at the thymine dimer site
AU643542B2 (en)	1993-11-18	RNA hydrolysis/cleavage
US20090286247A1 (en)	2009-11-19	Novel nucleic acid base pair
JPWO1987001373A1 (ja)	1987-06-04	オリゴまたはポリヌクレオチド
JPH03501128A (ja)	1991-03-14	ヌクレオシドおよびポリヌクレオチドチオホスホラミダイトおよびホスホロジチオエイト化合物並びに方法
US5204456A (en)	1993-04-20	Derivatives of nucleosides and their use for the synthesis of oligonucleotides
US5179200A (en)	1993-01-12	N4-(3-phenylproprionyl)-2'-deoxycytidine
US4503233A (en)	1985-03-05	Phosphorylating agent and process for the phosphorylation of organic hydroxyl compounds
US3755296A (en)	1973-08-28	Process for preparing 1-{62 -d-arabinofuranosyl-cytosine and 2,2{40 -cyclocytidine
JPS5841896A (ja)	1983-03-11	保護されたヌクレオチドを脱シアノエチル化する方法
Clivio et al.	1992	Synthesis of deoxydinucleoside phosphates containing 4-thio substituted pyrimidine nucleobases
IKEHARA et al.	1974	Polynucleotides. XXVI. Synthesis of an AUG Analog, 8, 2-Anhydro-8-oxy-9-β-D-arabinofuranosyladenine Phosphoryl-(3'-5')-uridylyl-(3'-5')-guanosine
CA1167032A (en)	1984-05-08	Nucleosidic coupling agent and methods
EP0698610B1 (de)	1998-08-12	Verfahren zur herstellung von sialinsäure-derivaten und neue sialinsäure-derivate
Sekine et al.	1988	Synthesis of oligoribonucleotides by use of 4, 4', 4"-tris (acyloxy) trityl groups for protection of the 6-amino group of adenosine.
Caruthers et al.	1987	Phosphoramidites as Synthons for Polynucleotide Synthesis
JPS61171497A (ja)	1986-08-02	ルア−・ヌクレオチド
JPH0372235B2 (de)	1991-11-18
Ogilvie	1968	A Triester Approach to Oligonucleotide Synthesis