KR970042582A - 6-isopropyldimethylsilyl-2,3-diethyl beta cyclodextrin useful for optical isomer separation and preparation method thereof - Google Patents

6-isopropyldimethylsilyl-2,3-diethyl beta cyclodextrin useful for optical isomer separation and preparation method thereof Download PDF

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KR970042582A
KR970042582A KR1019950056714A KR19950056714A KR970042582A KR 970042582 A KR970042582 A KR 970042582A KR 1019950056714 A KR1019950056714 A KR 1019950056714A KR 19950056714 A KR19950056714 A KR 19950056714A KR 970042582 A KR970042582 A KR 970042582A
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South Korea
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formula
derivative
isopropyldimethylsilyl
cyclodextrin
optical isomer
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KR1019950056714A
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Korean (ko)
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KR100217841B1 (en
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김병억
소재춘
우순형
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김종진
포항종합제철 주식회사
신창식
재단법인산업과학기술연구소
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Priority to KR1019950056714A priority Critical patent/KR100217841B1/en
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
    • C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
    • C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/08—Selective adsorption, e.g. chromatography
    • B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
    • B01D15/38—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving specific interaction not covered by one or more of groups B01D15/265 - B01D15/36
    • B01D15/3833—Chiral chromatography
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/281—Sorbents specially adapted for preparative, analytical or investigative chromatography
    • B01J20/29—Chiral phases

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  • Chemical & Material Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Biochemistry (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Molecular Biology (AREA)
  • General Health & Medical Sciences (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

본 발명은 β-시클로 덱스트린 유도체에 관한 것이며, 보다 상세하게는 광학 이성질체 분리에 유용한 β-시클로 덱스트린 유도체에 관한 것으로써, 6번 위치의 탄소에 이소프로필디메틸실릴기가 그리고 2,3번 위치에 에틸기가 도입된 하기 식(I)을 갖는 새로운 β-CD 유도체가 제공되며 이는 라세미 광학활성 물질의 분리에서 CGC컬럼의 정지상으로 사용된다.The present invention relates to β-cyclodextrin derivatives, and more particularly to β-cyclodextrin derivatives useful for optical isomer separation, wherein isopropyldimethylsilyl group is located at carbon at position 6 and an ethyl group is placed at positions 2 and 3. There is provided a new β-CD derivative having the following formula (I), which is used as the stationary phase of the CGC column in the separation of racemic optically active materials.

본 발명에는 상기와 같은 β-시클로덱스트린유도체를 제조하는 방법 및 이 같은 유도체를 이용하여 광학이성질체를 분리하는 방법이 또한 제공된다.The present invention also provides a method for preparing such β-cyclodextrin derivatives and a method for separating optical isomers using such derivatives.

Description

광학 이성질체 분리에 유용한 6-이소프로필디메틸실릴-2,3-디에틸 베타 시클로덱스트린 및 그 제조방법6-isopropyldimethylsilyl-2,3-diethyl beta cyclodextrin useful for optical isomer separation and preparation method thereof

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

제1도는 본 발명에 의한 β-시클로덱스트린 유도체를 이용하여 알코올 광학 이성질체를 분리한 기체 크로마토그램.1 is a gas chromatogram obtained by separating alcohol optical isomers using a β-cyclodextrin derivative according to the present invention.

Claims (5)

하기 구조식 (I)을 갖는 광학이성질체분리에 정지상으로 유용한 6-이소프로필 디메틸실릴-2,3-디에틸-시클로 덱스트린 화합물.6-isopropyl dimethylsilyl-2,3-diethyl-cyclodextrin compound useful as stationary phase for optical isomeric separation having formula (I) 하기 식(II)의 β-시클로덱스트린 화합물을 tert-부틸디메틸실릴 클로라이드와 반응시켜 하기 식(III)의 β-CD 실란 유도체를 형성하는단계 ; 상기 β-CD 실란 유도체와 요오드화 에탄을 알킬화 반응시켜 하기 식(IV)의 디알킬실란화된 β-CD 유도체를 형성하는단계 ; 하기 식(IV)의 유도체와 테트라부틸암모늄 플로라이드를 반응시켜 시클로덱스트린의 6번 탄소위치의 t-부틸디메틸실란기를 제거하는단계 ; 및 하기 식(V)의 t-부틸디메틸 실란기가 제거된 β-CD를 이소프로필디메틸실릴클로라이드와 반응시키는단계 ; 를 포함하는 상기 식(I)의 6-이소프로필디메틸실릴-2,3-디에틸-β-시클로덱스트린 제조 방법.Reacting the β-cyclodextrin compound of formula (II) with tert-butyldimethylsilyl chloride to form a β-CD silane derivative of formula (III); Alkylating the β-CD silane derivative with iodide ethane to form a dialkylsilaneated β-CD derivative of Formula (IV); Reacting a derivative of formula (IV) with tetrabutylammonium fluoride to remove the t-butyldimethylsilane group at the 6th carbon position of the cyclodextrin; And reacting β-CD from which the t-butyldimethyl silane group of formula (V) is removed with isopropyldimethylsilyl chloride; 6-isopropyldimethylsilyl-2,3-diethyl-β-cyclodextrin production method of formula (I) comprising a. (단, 식중에서 R은 CH2CH3이다. )(Wherein R is CH 2 CH 3 ) 정지상과 혼합물을 접촉시켜 광학이성질체를 분리하는 기체크로마토그피 분리방법에 있어서, 상기 정지상으로 청구범위 제1항 시클로덱스트린 유도체(식(I))를 사용함을 특징으로 하는 분리방법.A gas chromatographic separation method for separating an optical isomer by contacting a stationary phase with a mixture, wherein the separation phase is characterized by using the claim 1 cyclodextrin derivative (formula (I)) as the stationary phase. 제3항에 있어서, 상기 광학이성질체는 알코올임을 특징으로 하는 방법.The method of claim 3, wherein the optical isomer is an alcohol. 제4항에 있어서, 상기 알코올은 3-펜텐-2-올, 리모넨 및 페닐 에틸 프로피오네이트로 구성되는 그룹에서 선택됨을 특징으로 하는 방법.5. The method of claim 4, wherein the alcohol is selected from the group consisting of 3-penten-2-ol, limonene and phenyl ethyl propionate. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019950056714A 1995-12-26 1995-12-26 6-isopropyl dimetylsylil-2,3-diethyl beta cyclodextrin which is useful for separation of isomer and preparing method KR100217841B1 (en)

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KR1019950056714A KR100217841B1 (en) 1995-12-26 1995-12-26 6-isopropyl dimetylsylil-2,3-diethyl beta cyclodextrin which is useful for separation of isomer and preparing method

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KR1019950056714A KR100217841B1 (en) 1995-12-26 1995-12-26 6-isopropyl dimetylsylil-2,3-diethyl beta cyclodextrin which is useful for separation of isomer and preparing method

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