KR920021526A - 3-치환된 푸라노스 또는 푸라노시드 화합물을 제조하는 방법 - Google Patents
3-치환된 푸라노스 또는 푸라노시드 화합물을 제조하는 방법 Download PDFInfo
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- KR920021526A KR920021526A KR1019920007889A KR920007889A KR920021526A KR 920021526 A KR920021526 A KR 920021526A KR 1019920007889 A KR1019920007889 A KR 1019920007889A KR 920007889 A KR920007889 A KR 920007889A KR 920021526 A KR920021526 A KR 920021526A
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- 150000001875 compounds Chemical class 0.000 title claims abstract 11
- 150000002243 furanoses Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 9
- 239000001257 hydrogen Substances 0.000 claims abstract 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract 8
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract 4
- 150000002431 hydrogen Chemical group 0.000 claims abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract 3
- 150000002367 halogens Chemical class 0.000 claims abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 230000000269 nucleophilic effect Effects 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- DBYJIWYDEHDKJS-SNAWJCMRSA-N (2e)-hexa-2,5-dien-1-ol Chemical compound OC\C=C\CC=C DBYJIWYDEHDKJS-SNAWJCMRSA-N 0.000 claims 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims 2
- XEBCWEDRGPSHQH-YUMQZZPRSA-N dipropan-2-yl (2s,3s)-2,3-dihydroxybutanedioate Chemical compound CC(C)OC(=O)[C@@H](O)[C@H](O)C(=O)OC(C)C XEBCWEDRGPSHQH-YUMQZZPRSA-N 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- KSOMTIQGBYHOJM-UHFFFAOYSA-N hex-5-en-2-yn-1-ol Chemical compound OCC#CCC=C KSOMTIQGBYHOJM-UHFFFAOYSA-N 0.000 claims 2
- 239000012280 lithium aluminium hydride Substances 0.000 claims 2
- -1 lithium aluminum hydride Chemical compound 0.000 claims 2
- 229910052763 palladium Inorganic materials 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 claims 2
- 239000010936 titanium Substances 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- LCKIEQZJEYYRIY-UHFFFAOYSA-N Titanium ion Chemical compound [Ti+4] LCKIEQZJEYYRIY-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 150000001805 chlorine compounds Chemical group 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 230000000840 anti-viral effect Effects 0.000 abstract 1
- 230000004071 biological effect Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/20—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C247/00—Compounds containing azido groups
- C07C247/02—Compounds containing azido groups with azido groups bound to acyclic carbon atoms of a carbon skeleton
- C07C247/04—Compounds containing azido groups with azido groups bound to acyclic carbon atoms of a carbon skeleton being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C247/00—Compounds containing azido groups
- C07C247/02—Compounds containing azido groups with azido groups bound to acyclic carbon atoms of a carbon skeleton
- C07C247/08—Compounds containing azido groups with azido groups bound to acyclic carbon atoms of a carbon skeleton being unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/40—Halogenated unsaturated alcohols
- C07C33/42—Halogenated unsaturated alcohols acyclic
- C07C33/423—Halogenated unsaturated alcohols acyclic containing only double bonds as unsaturation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/14—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/003—Compounds containing elements of Groups 4 or 14 of the Periodic Table without C-Metal linkages
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H11/00—Compounds containing saccharide radicals esterified by inorganic acids; Metal salts thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
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- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/14—Acyclic radicals, not substituted by cyclic structures attached to a sulfur, selenium or tellurium atom of a saccharide radical
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
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- Genetics & Genomics (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Epoxy Compounds (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- 하기 a)-e)로 구성되는, 하기 일반식:(이때, M이 수소 또는 알킬(C1-C3), A가 할로겐 또는 하기 일반식:또는 CN(이때, R은 수소, 분지된 또는 비분지된 알킬(C1-C4) 또는 페닐이다.)의 부분으로부터 선택된 친핵성 치환체임)의 화합물을 제조하는 방법: a) X가 클로라이드 또는 브로마이드로서 정의되는 하기 일반식:의 화합물을 프로파르길 알코올과 반응시켜 헥스-5-엔-2-인-1-올을 형성시키고; b) 단계 a의 생성물을 리튬 알루미늄 수소화물과 반응시켜 2,5-헥사디엔-1-올을 형성하고; c) 디이소프로필-D-주석산염의 존재하에 단계 b의 생성물을 반응시켜 2R,3R-에폭시헥스-5-엔-1-올을 형성하고; d) 단계 c의 생성물을 친핵성 치환체 A를 가지는 적당한 시약과 반응시켜 하기 일반식의 화합물을 형성하고:e) 단계 d의 생성물을 오존과 반응시키고 나서 탄소-상-팔라듐상에서 수소로 촉매 환원시켜 하기 일반식의 화합물을 제공한다.:
- 제1항에 있어서. 단계 (d)의 적당한 시약이 일반식:Ti(OR′)nA4-n(이때, n이 1-3의 정수로 정의되고; R'가 분지된 또는 비분지된 알킬 (C1-C4)이고 A가 F, Cl, Br, I로서 정의되거나 하기 일반식:또는 CN(이때, R은 수소, 분지된 또는 비분지된 알킬(C1-C4) 또는 페닐이다)의 부분으로부터 선택될 수 있음)을 가지는 방법.
- 제2항에 있어서, R'가 이소프로필로서 정의되고, R은 2이고 A가 플루오르인 방법.
- 제2항에 있어서, R'가 이소프로필로서 정의되고 n이 1이고 A가 플루오르인 방법,
- 제2항에 있어서, R'가 이소프로필로서 정의되고 n은 1이고 A가 -N3인 방법.
- 2R,3R-에폭시헥스-5-엔-1-올 화합물.
- 2R,3S-3-플루오로헥스-5-엔-1,2-디올 화합물.
- 2R,3S-3-아지도헥스-5-엔-1,2-디올 화합물.
- 티타늄(Ⅳ) 디플루오로디이소프로폭시드 화합물.
- 하기 a)-e)로 구성되는, 하기 일반식:(이때, M이 수소 또는 알킬(C1-C3), A가 할로겐 또는 하기 일반식:또는 CN(이때, R은 수소, 분지된 또는 비분지된 알킬(C1-C4) 또는 페닐이다.)의 부분으로부터 선택된 친핵성 치환체임)의 화합물을 제조하는 방법:a) X가 클로라이드 또는 브로마이드로서 정의되는 하기 일반식:의 화합물을 프로파르길 알코올과 반응시켜 헥스-5-엔-2-인-1-올을 형성시키고; b) 단계 a의 생성물을 리튬 알루미늄 수소화물과 반응시켜 2,5-헥사디엔-1-올을 형성하고; c) 단계 b의 생성물을 -30℃― -20℃에서 8-10시간동안 디이소프로필-D-주석산염의 존재하에 반응시켜 2R,3R-에폭시헥스-5-엔-1-올을 형성하고; d)단계 c의 생성물을, n이 1-3의 정수이고; R'이 분지된 비분지된 알칼(C1-C4)이고 A가 상기 정의된 바와 같은 하기 일반식:Ti(OR′)nA4-n의 시약과 반응시켜 하기 일반식으로 화합물을 형성하고,e) 단계 d의 생성물을 오존과 반응시키고 나서 탄소-상-팔라듐상에서 수소로 촉매 환원시켜 하기 일반식의 화합물을 얻는다.:※ 참고사항 : 최초출원 내용에 의하여 공개되는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/698,042 | 1991-05-10 | ||
| US07/698,042 US5216145A (en) | 1991-05-10 | 1991-05-10 | Asymmetric synthesis of 3-substituted furanoside compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR920021526A true KR920021526A (ko) | 1992-12-18 |
Family
ID=24803685
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019920007889A KR920021526A (ko) | 1991-05-10 | 1992-05-09 | 3-치환된 푸라노스 또는 푸라노시드 화합물을 제조하는 방법 |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US5216145A (ko) |
| EP (1) | EP0540807B1 (ko) |
| JP (1) | JPH05170782A (ko) |
| KR (1) | KR920021526A (ko) |
| CN (1) | CN1032062C (ko) |
| AT (1) | ATE132125T1 (ko) |
| AU (1) | AU657129B2 (ko) |
| CA (1) | CA2068226A1 (ko) |
| CZ (1) | CZ283306B6 (ko) |
| DE (1) | DE69207154T2 (ko) |
| DK (1) | DK0540807T3 (ko) |
| ES (1) | ES2083608T3 (ko) |
| FI (1) | FI922097A (ko) |
| GR (1) | GR3018671T3 (ko) |
| HU (1) | HU209838B (ko) |
| IE (1) | IE75888B1 (ko) |
| IL (3) | IL101799A (ko) |
| NO (1) | NO178113C (ko) |
| NZ (1) | NZ242639A (ko) |
| PH (1) | PH31630A (ko) |
| PL (1) | PL168588B1 (ko) |
| SK (1) | SK279311B6 (ko) |
| TW (1) | TW223068B (ko) |
| ZA (1) | ZA923350B (ko) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5216145A (en) * | 1991-05-10 | 1993-06-01 | American Cyanamid Company | Asymmetric synthesis of 3-substituted furanoside compounds |
| US5521294A (en) * | 1995-01-18 | 1996-05-28 | Eli Lilly And Company | 2,2-difluoro-3-carbamoyl ribose sulfonate compounds and process for the preparation of beta nucleosides |
| EP1812457A1 (en) * | 2004-07-30 | 2007-08-01 | Pharmaessentia Corp. | STEREOSELECTIVE SYNTHESIS OF ß-NUCLEOSIDES |
| US7485716B2 (en) * | 2005-05-02 | 2009-02-03 | Pharmaessentia Corp. | Stereoselective synthesis of β-nucleosides |
| CN101883570B (zh) * | 2007-11-06 | 2013-06-19 | 药华医药股份有限公司 | β-核苷的新颖合成 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5216145A (en) * | 1991-05-10 | 1993-06-01 | American Cyanamid Company | Asymmetric synthesis of 3-substituted furanoside compounds |
-
1991
- 1991-05-10 US US07/698,042 patent/US5216145A/en not_active Expired - Fee Related
-
1992
- 1992-03-16 AT AT92104485T patent/ATE132125T1/de not_active IP Right Cessation
- 1992-03-16 DE DE69207154T patent/DE69207154T2/de not_active Expired - Fee Related
- 1992-03-16 ES ES92104485T patent/ES2083608T3/es not_active Expired - Lifetime
- 1992-03-16 DK DK92104485.5T patent/DK0540807T3/da active
- 1992-03-16 EP EP92104485A patent/EP0540807B1/en not_active Expired - Lifetime
- 1992-03-17 TW TW081102018A patent/TW223068B/zh active
- 1992-04-11 CN CN92102690A patent/CN1032062C/zh not_active Expired - Fee Related
- 1992-05-06 JP JP4139628A patent/JPH05170782A/ja active Pending
- 1992-05-06 IL IL101799A patent/IL101799A/en not_active IP Right Cessation
- 1992-05-06 IL IL11697192A patent/IL116971A/xx not_active IP Right Cessation
- 1992-05-07 SK SK1386-92A patent/SK279311B6/sk unknown
- 1992-05-07 CZ CS921386A patent/CZ283306B6/cs not_active IP Right Cessation
- 1992-05-07 NZ NZ242639A patent/NZ242639A/en unknown
- 1992-05-08 CA CA002068226A patent/CA2068226A1/en not_active Abandoned
- 1992-05-08 FI FI922097A patent/FI922097A/fi unknown
- 1992-05-08 HU HU9201546A patent/HU209838B/hu not_active IP Right Cessation
- 1992-05-08 NO NO921837A patent/NO178113C/no not_active IP Right Cessation
- 1992-05-08 PL PL92294479A patent/PL168588B1/pl unknown
- 1992-05-08 AU AU16132/92A patent/AU657129B2/en not_active Ceased
- 1992-05-08 ZA ZA923350A patent/ZA923350B/xx unknown
- 1992-05-09 KR KR1019920007889A patent/KR920021526A/ko not_active Application Discontinuation
- 1992-07-01 IE IE921483A patent/IE75888B1/en not_active IP Right Cessation
-
1993
- 1993-03-12 US US08/031,304 patent/US5296620A/en not_active Expired - Lifetime
-
1995
- 1995-01-10 PH PH49766A patent/PH31630A/en unknown
-
1996
- 1996-01-16 GR GR950402590T patent/GR3018671T3/el unknown
- 1996-01-30 IL IL11697196A patent/IL116971A0/xx unknown
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