JPH0253411B2 - - Google Patents

Info

Publication number: JPH0253411B2
Authority: JP; Japan
Prior art keywords: group; compound; cram; formula; carbon atoms
Prior art date: 1985-08-29
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.): Expired - Lifetime

Application number

JP60188483A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6251628A (ja

Inventor

Yoshinori Yamamoto

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.)

Teijin Ltd

Original Assignee

Teijin Ltd

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.)

1985-08-29

Filing date

1985-08-29

Publication date

1990-11-16

1985-08-29 Application filed by Teijin Ltd filed Critical Teijin Ltd

1985-08-29 Priority to JP60188483A priority Critical patent/JPS6251628A/ja

1987-03-06 Publication of JPS6251628A publication Critical patent/JPS6251628A/ja

1990-11-16 Publication of JPH0253411B2 publication Critical patent/JPH0253411B2/ja

Status Granted legal-status Critical Current

Links

DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 18
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 17
125000004432 carbon atom Chemical group C* 0.000 claims description 15
150000002440 hydroxy compounds Chemical class 0.000 claims description 14
150000002902 organometallic compounds Chemical class 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 8
239000012442 inert solvent Substances 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
125000000962 organic group Chemical group 0.000 claims description 3
125000001183 hydrocarbyl group Chemical group 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
238000000034 method Methods 0.000 description 17
150000001875 compounds Chemical class 0.000 description 11
150000003431 steroids Chemical group 0.000 description 10
238000003786 synthesis reaction Methods 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
125000003172 aldehyde group Chemical group 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
IXVMHGVQKLDRKH-VRESXRICSA-N Brassinolide Natural products O=C1OC[C@@H]2[C@@H]3[C@@](C)([C@H]([C@@H]([C@@H](O)[C@H](O)[C@H](C(C)C)C)C)CC3)CC[C@@H]2[C@]2(C)[C@@H]1C[C@H](O)[C@H](O)C2 IXVMHGVQKLDRKH-VRESXRICSA-N 0.000 description 5
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
IXVMHGVQKLDRKH-KNBKMWSGSA-N brassinolide Chemical compound C1OC(=O)[C@H]2C[C@H](O)[C@H](O)C[C@]2(C)[C@H]2CC[C@]3(C)[C@@H]([C@H](C)[C@@H](O)[C@H](O)[C@@H](C)C(C)C)CC[C@H]3[C@@H]21 IXVMHGVQKLDRKH-KNBKMWSGSA-N 0.000 description 5
239000002904 solvent Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
239000002994 raw material Substances 0.000 description 4
239000002841 Lewis acid Substances 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
150000002430 hydrocarbons Chemical group 0.000 description 3
150000007517 lewis acids Chemical class 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000007800 oxidant agent Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
239000000126 substance Substances 0.000 description 3
-1 verklein Chemical compound 0.000 description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000000605 extraction Methods 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
150000002642 lithium compounds Chemical class 0.000 description 2
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000000203 mixture Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000007858 starting material Substances 0.000 description 2
150000003505 terpenes Chemical group 0.000 description 2
JGVXQQVUKNOCDJ-UHFFFAOYSA-N 4-methylbenzenesulfonate pyridin-1-ium Chemical compound c1cc[nH+]cc1.c1cc[nH+]cc1.Cc1ccc(cc1)S([O-])(=O)=O.Cc1ccc(cc1)S([O-])(=O)=O JGVXQQVUKNOCDJ-UHFFFAOYSA-N 0.000 description 1
102000018997 Growth Hormone Human genes 0.000 description 1
108010051696 Growth Hormone Proteins 0.000 description 1
BUIQRTDBPCHRIR-UHFFFAOYSA-L O[Cr](Cl)(=O)=O Chemical compound O[Cr](Cl)(=O)=O BUIQRTDBPCHRIR-UHFFFAOYSA-L 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
229910003074 TiCl4 Inorganic materials 0.000 description 1
MWOQRLMTLAHNFB-UHFFFAOYSA-N [Li]C#CC(C)C Chemical compound [Li]C#CC(C)C MWOQRLMTLAHNFB-UHFFFAOYSA-N 0.000 description 1
230000002411 adverse Effects 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
229950005228 bromoform Drugs 0.000 description 1
INGGGNUCWJHFKD-UHFFFAOYSA-N chromium;pyridine Chemical compound [Cr].C1=CC=NC=C1 INGGGNUCWJHFKD-UHFFFAOYSA-N 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000122 growth hormone Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
150000003961 organosilicon compounds Chemical class 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen 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
230000008635 plant growth Effects 0.000 description 1
239000003375 plant hormone Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
239000002699 waste material Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Landscapes

Steroid Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

JP60188483A 1985-08-29 1985-08-29 ヒドロキシ化合物の製造法 Granted JPS6251628A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP60188483A JPS6251628A (ja)	1985-08-29	1985-08-29	ヒドロキシ化合物の製造法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP60188483A JPS6251628A (ja)	1985-08-29	1985-08-29	ヒドロキシ化合物の製造法

Publications (2)

Publication Number	Publication Date
JPS6251628A JPS6251628A (ja)	1987-03-06
JPH0253411B2 true JPH0253411B2 (fr)	1990-11-16

Family

ID=16224519

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP60188483A Granted JPS6251628A (ja)	1985-08-29	1985-08-29	ヒドロキシ化合物の製造法

Country Status (1)

Country	Link
JP (1)	JPS6251628A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH06263652A (ja) *	1993-03-11	1994-09-20	Central Glass Co Ltd	光学活性なハロゲン化ヒドロキシオレフィン類の製造方法

1985
- 1985-08-29 JP JP60188483A patent/JPS6251628A/ja active Granted

Also Published As

Publication number	Publication date
JPS6251628A (ja)	1987-03-06

Publication	Publication Date	Title
Ibuka et al.	1989	Very high chemoselective, regioselective, and E-stereoselective 1, 3-chirality transfer involving reaction of acyclic (E)-and (Z)-. gamma.-mesyloxy. alpha.,. beta.-enoates and organocyanocopper-trifluoroborane reagents. Efficient synthetic routes to functionalized chiral. alpha.-alkyl (E)-. beta.,. gamma.-enoates and (E)-allylic alcohols with high optical purity
DE68909166T2 (de)	1994-02-10	Verfahren zur Herstellung von in 5-Stellung substituierten 3-Furaldehyden.
Birch et al.	1982	Organometallic compounds in organic synthesis—part 17: Reactions of tricarbonylcyclohexadienyliron salts with o-silylated enolates, allyl silanes and aspects of their synthetic equivalents
JPH0253411B2 (fr)	1990-11-16
JPH0253412B2 (fr)	1990-11-16
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EP0247740A2 (fr)	1987-12-02	Isocarbacyclines et leurs procédés de production
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JP2713333B2 (ja)	1998-02-16	イソカルバサイクリン類及びその製造法
JPH0316354B2 (fr)	1991-03-05
JPS637170B2 (fr)	1988-02-15
JP2703392B2 (ja)	1998-01-26	イソカルバサイクリン類の製造法
JP2731013B2 (ja)	1998-03-25	１１―エピイソカルバサイクリン類およびその製造法
JPH0386840A (ja)	1991-04-11	α，β―不飽和カルボニル化合物の製造方法
FR2574406A1 (fr)	1986-06-13	Nouveaux derives de pyrrolo-pyridine, leurs procedes de preparation ainsi que leurs applications
JPH0220616B2 (fr)	1990-05-10
JPH0660155B2 (ja)	1994-08-10	イソカルバサイクリン類
JPS5944336A (ja)	1984-03-12	２−アリルシクロペンタノン類の新規製造法
JPH0565242A (ja)	1993-03-19	アリルアルコール体およびその製造方法
JPS626551B2 (fr)	1987-02-12