JPH0113725B2 - - Google Patents

Info

Publication number: JPH0113725B2
Authority: JP; Japan
Prior art keywords: cyclodextrin; trityl; mixture; water; tritylated
Prior art date: 1985-05-20
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

Application number

JP10788285A

Other languages

English (en)

Japanese (ja)

Other versions

JPS61266401A (ja

Inventor

Teiichi Murakami

Kazuaki Harada

Satoshi Morimoto

Keishiro Tsuda

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.)

National Institute of Advanced Industrial Science and Technology AIST

Original Assignee

Agency of Industrial Science and Technology

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.)

1985-05-20

Filing date

1985-05-20

Publication date

1989-03-08

1985-05-20 Application filed by Agency of Industrial Science and Technology filed Critical Agency of Industrial Science and Technology

1985-05-20 Priority to JP10788285A priority Critical patent/JPS61266401A/ja

1986-11-26 Publication of JPS61266401A publication Critical patent/JPS61266401A/ja

1989-03-08 Publication of JPH0113725B2 publication Critical patent/JPH0113725B2/ja

Status Granted legal-status Critical Current

Links

229920000858 Cyclodextrin Polymers 0.000 claims description 71
239000001116 FEMA 4028 Substances 0.000 claims description 44
229960004853 betadex Drugs 0.000 claims description 44
WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims description 33
235000011175 beta-cyclodextrine Nutrition 0.000 claims description 31
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 30
239000000203 mixture Substances 0.000 claims description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical group CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 10
-1 trityl halide Chemical class 0.000 claims description 10
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
239000012046 mixed solvent Substances 0.000 claims description 7
239000003125 aqueous solvent Substances 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 19
239000000047 product Substances 0.000 description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
239000007787 solid Substances 0.000 description 12
150000001875 compounds Chemical class 0.000 description 11
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 11
239000000126 substance Substances 0.000 description 11
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 11
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
229940097362 cyclodextrins Drugs 0.000 description 8
108090000790 Enzymes Proteins 0.000 description 7
102000004190 Enzymes Human genes 0.000 description 7
229940088598 enzyme Drugs 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
238000003756 stirring Methods 0.000 description 6
230000003197 catalytic effect Effects 0.000 description 5
239000007788 liquid Substances 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 5
238000000354 decomposition reaction Methods 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
230000000704 physical effect Effects 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
229920001450 Alpha-Cyclodextrin Polymers 0.000 description 3
229940043377 alpha-cyclodextrin Drugs 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
125000000524 functional group Chemical group 0.000 description 3
125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
150000003222 pyridines Chemical class 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
239000000243 solution Substances 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical group NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
230000000087 stabilizing effect Effects 0.000 description 2
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
125000002353 D-glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
102000003929 Transaminases Human genes 0.000 description 1
108090000340 Transaminases Proteins 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
108010027597 alpha-chymotrypsin Proteins 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000012237 artificial material Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000013305 food Nutrition 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
230000001035 methylating effect Effects 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229920001542 oligosaccharide Polymers 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
238000006557 surface reaction Methods 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
238000005866 tritylation reaction Methods 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1

Landscapes

Polysaccharides And Polysaccharide Derivatives (AREA)

JP10788285A 1985-05-20 1985-05-20 トリチル化β−シクロデキストリン及びその製造方法 Granted JPS61266401A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP10788285A JPS61266401A (ja)	1985-05-20	1985-05-20	トリチル化β−シクロデキストリン及びその製造方法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP10788285A JPS61266401A (ja)	1985-05-20	1985-05-20	トリチル化β−シクロデキストリン及びその製造方法

Publications (2)

Publication Number	Publication Date
JPS61266401A JPS61266401A (ja)	1986-11-26
JPH0113725B2 true JPH0113725B2 (da)	1989-03-08

Family

ID=14470473

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP10788285A Granted JPS61266401A (ja)	1985-05-20	1985-05-20	トリチル化β−シクロデキストリン及びその製造方法

Country Status (1)

Country	Link
JP (1)	JPS61266401A (da)

1985
- 1985-05-20 JP JP10788285A patent/JPS61266401A/ja active Granted

Also Published As

Publication number	Publication date
JPS61266401A (ja)	1986-11-26

Legal Events

Date	Code	Title	Description
2005-05-20	EXPY	Cancellation because of completion of term

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