KR940000474A - Method for preparing 2-deoxy-2, 2-difluoro-D-ribofuranosylsulfonate rich in alpha-anomer - Google Patents

Method for preparing 2-deoxy-2, 2-difluoro-D-ribofuranosylsulfonate rich in alpha-anomer Download PDF

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Publication number
KR940000474A
KR940000474A KR1019930011309A KR930011309A KR940000474A KR 940000474 A KR940000474 A KR 940000474A KR 1019930011309 A KR1019930011309 A KR 1019930011309A KR 930011309 A KR930011309 A KR 930011309A KR 940000474 A KR940000474 A KR 940000474A
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Prior art keywords
acid
sulfonate
group
ribofuranosyl
methanesulfonate
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KR1019930011309A
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Korean (ko)
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초우 타-센
데이비드 존스 챨스
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리로이 휘테커
일라이 릴리 앤드 캄파니
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Priority claimed from US07/902,301 external-priority patent/US5401861A/en
Priority claimed from US07/902,305 external-priority patent/US5256798A/en
Application filed by 리로이 휘테커, 일라이 릴리 앤드 캄파니 filed Critical 리로이 휘테커
Publication of KR940000474A publication Critical patent/KR940000474A/en

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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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Saccharide Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

본 발명은 베타-아노머 리보푸라노실 설포네이트 또는 그의 아노머 혼합물을 불활성 용매중 승온에서 설폰산의 공액 음이온 공급원으로 처리함을 포함하는, 베타-아노머 리보푸라노실 설포네이트로 부터 알파-아노머가 풍부한 리보푸라노실 설포네이트를 제조하는 방법을 제공한다.The present invention relates to alpha-ano from beta-anomeric ribofuranosyl sulfonate, comprising treating a beta-anomeric ribofuranosyl sulfonate or an anomer mixture thereof with a conjugated anion source of sulfonic acid at elevated temperature in an inert solvent. Provided are methods for making merborich rich ribofuranosyl sulfonates.

Description

알파-아노머가 풍부한 2-데옥시-2,2-디플루오로-D-리보푸라노실 설포네이트의 제조방법Process for preparing 2-deoxy-2,2-difluoro-D-ribofuranosyl sulfonate rich in alpha-anomer

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

Claims (9)

하기 일반식(Ⅱ)의 베타-아노머 리보푸라노실 설포네이트를 불활성 용매중 승온에서 설폰산의 공액 음이온의 공급원으로 처리함을 포함하는, 하기 일반식 (Ⅱ)의 베타-아노머 리보푸라노실 설포네이트로 부터의 하기 일반식 (I)의 알파-아노머가 풍부한 리보푸라노실 설포네이트의 제조방법 :Beta-anomeric ribofuranosyl of formula (II) comprising treating the beta-anomeric ribofuranosyl sulfonate of formula (II) with a source of conjugated anion of sulfonic acid at elevated temperature in an inert solvent Process for preparing ribofuranosyl sulfonate rich in alpha-anomer of the general formula (I) from sulfonate: 상기식에서, Y는 설포네이트이고, X는 각각 독립적으로 하이드록시 보호 그룹중에서 선택된다.Wherein Y is a sulfonate and each X is independently selected from a hydroxy protecting group. 제1항에 있어서, Y가 메탄설포닐, 2-클로로-1-에탄설포닐, 톨루엔설포닐, p-니트로벤젠설포닐 및 p-브로모벤젠설포닐로 이루어진 그룹중에서 선택되는 방법.The process of claim 1 wherein Y is selected from the group consisting of methanesulfonyl, 2-chloro-1-ethanesulfonyl, toluenesulfonyl, p-nitrobenzenesulfonyl and p-bromobenzenesulfonyl. 제1항에 있어서, 상기 설폰산의 공액 음이온이 메탄설폰산, 에탄설폰산, 톨루엔설폰산, 1-프로판설폰산, p-클로로벤젠설폰산, p-브로모벤젠설폰산, 벤젠설폰산 및 캄포르설폰산의 알칼리 금속 염으로 이루어진 그룹 중에서 선택되는 방법.The method of claim 1, wherein the conjugated anion of sulfonic acid is methanesulfonic acid, ethanesulfonic acid, toluenesulfonic acid, 1-propanesulfonic acid, p-chlorobenzenesulfonic acid, p-bromobenzenesulfonic acid, benzenesulfonic acid and The process is selected from the group consisting of alkali metal salts of camphorsulfonic acid. 제3항에 있어서, 상기 설폰산의 공액 음이온이 트리에틸암모늄 메탄설포네이트, 트리메틸암모늄 메탄설포네이트, N,N-디메틸벤질암모늄 메탄설포네이트, 트리에틸암모늄(p-클로로벤젠)설포네이트, 트리에틸암모늄 (p-브로모벤젠)설포네이트, 피리디늄 메탄설포네이트, 테트라에틸암모늄 (p-톨루엔)설포네이트, 피리디늄 톨루엔설포네이트 및 피리디늄 니트로벤젠설포네이트의 아민 염으로 이루어진 그룹중에서 선택되는 방법.The method of claim 3, wherein the conjugated anion of sulfonic acid is triethylammonium methanesulfonate, trimethylammonium methanesulfonate, N, N-dimethylbenzylammonium methanesulfonate, triethylammonium (p-chlorobenzene) sulfonate, tri Selected from the group consisting of amine salts of ethylammonium (p-bromobenzene) sulfonate, pyridinium methanesulfonate, tetraethylammonium (p-toluene) sulfonate, pyridinium toluenesulfonate and pyridinium nitrobenzenesulfonate Way. 제1항에 있어서, 상기 설폰산의 공액 음이온이 2-데옥시-2,2-디플루오로-D-리보푸라노즈를 트리에틸민과 같은 염기중에서 설폰산 무수물과 반응시켜 동일반응계내에서 생성되는 방법.The conjugated anion of sulfonic acid is produced in situ by reacting 2-deoxy-2,2-difluoro-D-ribofuranose with sulfonic anhydride in a base such as triethylamine. How to be. 제1항에 있어서, X가 일치환된 벤조일, 이치환된 벤조일 및 벤조일로 이루어진 그룹중에서 선택되는 방법.The method of claim 1 wherein X is selected from the group consisting of monosubstituted benzoyl, disubstituted benzoyl and benzoyl. 제1항에 있어서, 상기 용매가 방향족 용매, 할로알킬 용매, 치환된 방향족 용매 및 그의 혼합물로 이루어진 그룹중에서 선택되는 방법.The method of claim 1 wherein said solvent is selected from the group consisting of aromatic solvents, haloalkyl solvents, substituted aromatic solvents, and mixtures thereof. 제1항에 있어서, 온도가 약 50℃ 내지 약 130℃인 방법.The method of claim 1 wherein the temperature is from about 50 ° C. to about 130 ° C. 7. 제1항 있어서, 상 전이 촉매 및 크라운 에테르 촉매증에서 선택된 촉매를 첨가함을 포함하는 방법.The method of claim 1 comprising adding a catalyst selected from a phase transfer catalyst and a crown ether catalysis. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019930011309A 1992-06-22 1993-06-21 Method for preparing 2-deoxy-2, 2-difluoro-D-ribofuranosylsulfonate rich in alpha-anomer KR940000474A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US07/902,301 US5401861A (en) 1992-06-22 1992-06-22 Low temperature process for preparing alpha-anomer enriched 2-deoxy-2,2-difluoro-D-ribofuranosyl sulfonates
US07/902,305 US5256798A (en) 1992-06-22 1992-06-22 Process for preparing alpha-anomer enriched 2-deoxy-2,2-difluoro-D-ribofuranosyl sulfonates
US902,301 1992-06-22
US902,305 1992-06-22

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR200458229Y1 (en) * 2009-12-29 2012-01-30 박종병 Connector for tractor operation machine

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR200458229Y1 (en) * 2009-12-29 2012-01-30 박종병 Connector for tractor operation machine

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