KR840005737A - Method for preparing 28-methyl-brasinosteroid derivatives - Google Patents

Method for preparing 28-methyl-brasinosteroid derivatives Download PDF

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KR840005737A
KR840005737A KR1019830004316A KR830004316A KR840005737A KR 840005737 A KR840005737 A KR 840005737A KR 1019830004316 A KR1019830004316 A KR 1019830004316A KR 830004316 A KR830004316 A KR 830004316A KR 840005737 A KR840005737 A KR 840005737A
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cholestan
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케르프 울리히 (외 2)
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게르하르트 리트케, 페터 헉스
쉐링 아크티엔 게젤샤프트
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J3/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J73/00—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms
    • C07J73/001—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms by one hetero atom
    • C07J73/003—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms by one hetero atom by oxygen as hetero atom
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N49/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing the group, wherein m+n>=1, both X together may also mean —Y— or a direct carbon-to-carbon bond, and the carbon atoms marked with an asterisk are not part of any ring system other than that which may be formed by the atoms X, the carbon atoms in square brackets being part of any acyclic or cyclic structure, or the group, wherein A means a carbon atom or Y, n>=0, and not more than one of these carbon atoms being a member of the same ring system, e.g. juvenile insect hormones or mimics thereof

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  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

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Description

28-메틸-브라시노스테로이드 유도체의 제조방법Method for preparing 28-methyl-brasinosteroid derivatives

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음As this is a public information case, the full text was not included.

Claims (45)

일반식(Ⅱ)의 화합물을, 필요하면 촉매존재하에 카복실산 무수물과 반응시킴을 특징으로 하여 일반식(Ⅰ) 화합물을 제조하는 방법.A process for preparing the compound of formula (I), wherein the compound of formula (II) is reacted with carboxylic anhydride in the presence of a catalyst if necessary. 상기 식에서,Where Z는 다음 그룹을 나타내며,R2, R3및 R22는 각각 수소원자 또는 아실그룹을 나타내고, 단, R2, R3및 R22중 적어도 하나는 아실그룹을 나타낸다.Z represents the next group, R 2 , R 3 and R 22 each represent a hydrogen atom or an acyl group, provided that at least one of R 2 , R 3 and R 22 represents an acyl group. 일반식(Ⅱa) 화합물을, 보론 트리플루오라이드에테레이트(필요하면 유기용매에 용해한); 유기용매에 용해한 오르토아세트산 트리에틸에스테르(필요하면 촉매 존재하에); 퍼클로르산중 아세토페논; 또는 디에틸카보네이트 및 촉매량의 나트룸 메톡사이드와 반응시킴을 특징으로 하여, 일반식(Ⅰ)화합물을 제조하는 방법.Boron trifluoride etherate (dissolved in an organic solvent, if necessary); Orthoacetic acid triethyl ester dissolved in an organic solvent (if necessary in the presence of a catalyst); Acetophenone in perchloric acid; Or reacting with diethyl carbonate and a catalytic amount of nathrum methoxide to produce a compound of formula (I). 상기 식에서,Where Z는그룹을 나타내며, R22는 수소원자 또는 아실그룹을 나타내고, 단, R2,및 R3함께그룹을 나타내며, X는 수소원자, C1-C4- 알킬그룹, 염소화, C1-C4- 알킬그룹, 또는 C1-C3- 알콕시그룹을 나타내고, Y는 수소원자, C2-C4- 알킬그룹, 염소화, C1-C4- 알킬그룹 또는 C1-C3- 알콕시그룹 또는 비치환되거나 치환된 아릴그룹을 나타내며, R22'는 수소원자 또는 아실그룹을 나타낸다.Z is R 22 represents a hydrogen atom or an acyl group, provided that R 2 , and R 3 together Represents a group, X represents a hydrogen atom, C 1 -C 4 -alkyl group, chlorination, C 1 -C 4 -alkyl group, or C 1 -C 3 -alkoxy group, Y is a hydrogen atom, C 2 -C 4 -alkyl group, chlorinated, C 1 -C 4 -alkyl group or C 1 -C 3 -alkoxy group or unsubstituted or substituted aryl group, R 22 ′ represents a hydrogen atom or an acyl group. 제1 또는 제2항에 있어서, 실제로 명세서에 기술된대로 수행되는 방법.The method of claim 1 or 2, which is actually performed as described in the specification. 제1 또는 제2항에 있어서, Z는 전기한 바와 같으며, R2,R3및 R22각각 수소원자 또는 포르밀그룹, C2-C7- 알킬-CC-그룹, C2-C7- 알콕시-C|1-C3- 알킬-CO-그룹, 아릴-CO-그룹 및 R2및 R3는 함께또는그룹을 나타내고, X는 수소원자, C1-C4- 알킬그룹, 염소화 C1-C4- 알킬그룹, 또는 C1-C3- 알콕시그룹을 나타내며, Y는 수소원자, C1-C4- 알킬그룹, 염소화 C1-C4- 알킬그룹, C1-C3- 알콕시그룹 또는 비치환되거나 치환된 아릴그룹을 나타내는 일반식(Ⅰ)화합물를 제조하는 방법.3. Z according to claim 1, wherein Z is as defined above, and R 2 , R 3 and R 22 are each hydrogen or formyl group, C 2 -C 7 -alkyl-CC-group, C 2 -C 7 Alkoxy-C | 1- C 3 -alkyl-CO-group, aryl-CO-group and R 2 and R 3 together or A group, X represents a hydrogen atom, a C 1 -C 4 -alkyl group, a chlorinated C 1 -C 4 -alkyl group, or a C 1 -C 3 -alkoxy group, Y is a hydrogen atom, C 1 -C 4 A process for preparing a compound of formula (I) representing an alkyl group, a chlorinated C 1 -C 4 -alkyl group, a C 1 -C 3 -alkoxy group or an unsubstituted or substituted aryl group. 제1항에 있어서, 2α-아세톡시-3α,22S, 23S - 트리하이드록시-24-에틸-7-옥사-B-호모-5α콜레스탄-6-온을 제조하는 방법.The method of claim 1, wherein 2α-acetoxy-3α, 22S, 23S-trihydroxy-24-ethyl-7-oxa-B-homo-5αcholestan-6-one is prepared. 제1항에 있어서,2α,22S,-디아세톡시-3α,23S-디하이드록시-24-에틸-7-옥사-B-호모-5α콜레스탄-6-온을 제조하는 방법.The method of claim 1, wherein 2α, 22S, -diacetoxy-3α, 23S-dihydroxy-24-ethyl-7-oxa-B-homo-5αcholestan-6-one is prepared. 제1항에 있어서, 2α-아세톡시-3α,22R, 23R - 트리하이드록시-24-에틸-7-옥사-B-호모-5α-콜레스탄-6-온을 제조하는 방법.The process of claim 1, wherein 2α-acetoxy-3α, 22R, 23R-trihydroxy-24-ethyl-7-oxa-B-homo-5α-cholestan-6-one is prepared. 제1항에 있어서, 2α-아세톡시-3α,22S, 23S - 트리하이드록시-24-에틸-6-옥사-B-호모-5α콜레스탄-7-온을 제조하는 방법.The method of claim 1, wherein 2α-acetoxy-3α, 22S, 23S-trihydroxy-24-ethyl-6-oxa-B-homo-5α cholestan-7-one is prepared. 제1항에 있어서,2α,22S,-디아세톡시-3α,23S-디하이드록시-24-에틸-6-옥사-B-호모-5α-콜레스탄-7-온을 제조하는 방법.The method of claim 1, wherein 2α, 22S, -diacetoxy-3α, 23S-dihydroxy-24-ethyl-6-oxa-B-homo-5α-cholestan-7-one is prepared. 제1항에 있어서, 2β-아세톡시-3β,22S, 23S - 트리하이드록시-24-에틸-7-옥사-B-호모-5α-콜레스탄-6-온을 제조하는 방법.The method of claim 1, wherein 2β-acetoxy-3β, 22S, 23S-trihydroxy-24-ethyl-7-oxa-B-homo-5α-cholestan-6-one is prepared. 제1항에 있어서, 2α-발레릴옥시-3α,22S, 23S-트리하이드록시-24-에틸-7-옥사-B-호모-5α-콜레스탄-6-온을 제조하는 방법.The method of claim 1, wherein 2α-valeryloxy-3α, 22S, 23S-trihydroxy-24-ethyl-7-oxa-B-homo-5α-cholestan-6-one is prepared. 제1항에 있어서, 2α-헵타노일옥시-3α,22R, 23R - 트리하이드록시-24-에틸-7-옥사-B-호모-5α-콜레스탄-6-온을 제조하는 방법.The method of claim 1, wherein 2α-heptanoyloxy-3α, 22R, 23R-trihydroxy-24-ethyl-7-oxa-B-homo-5α-cholestan-6-one is prepared. 제1항에 있어서, 2α-디메틸아세톡시-3α,22S, 23S -트리하이드록시-24-에틸The method of claim 1, wherein 2α-dimethylacetoxy-3α, 22S, 23S-trihydroxy-24-ethyl -7-옥사-B-호모-5α-콜레스탄-6-온을 제조하는 방법.A process for preparing -7-oxa-B-homo-5α-cholestan-6-one. 제1항에 있어서, 2α-부티릴옥시-3α,22S, 23S -트리하이드록시-24-에틸-6-옥사-B-호모-5α-콜레스탄-7-온을 제조하는 방법.The method of claim 1, wherein 2α-butyryloxy-3α, 22S, 23S-trihydroxy-24-ethyl-6-oxa-B-homo-5α-cholestan-7-one is prepared. 제1항에 있어서, 2α-디에틸아세톡시-3α,22S, 23S -트리하이드록시-24-에틸The method of claim 1, wherein 2α-diethylacetoxy-3α, 22S, 23S-trihydroxy-24-ethyl -7-옥사-B-호모-5α-콜레스탄-6-온을 제조하는 방법.A process for preparing -7-oxa-B-homo-5α-cholestan-6-one. 제1항에 있어서, 2α,3α-디발레릴옥시-22S,23S -디하이드록시-24-에틸-7-옥사-B-호모-5α-콜레스탄-6-온을 제조하는 방법.The process of claim 1, wherein 2α, 3α-divaleryloxy-22S, 23S-dihydroxy-24-ethyl-7-oxa-B-homo-5α-cholestan-6-one is prepared. 제1항에 있어서, 2α,22S-디발레릴옥시-3a,23S -디하이드록시-24-에틸-7-옥사-B-호모-5α-콜레스탄-6-온을 제조하는 방법.The method of claim 1, wherein 2α, 22S-divaleryloxy-3a, 23S-dihydroxy-24-ethyl-7-oxa-B-homo-5α-cholestan-6-one is prepared. 제1항에 있어서, 2α-에톡시아세톡시- 3α,22R,23R -디하이드록시-24-에틸-7-옥사-B-호모-5α-콜레스탄-6-온을 제조하는 방법.The process of claim 1, wherein 2α-ethoxyacetoxy-3α, 22R, 23R-dihydroxy-24-ethyl-7-oxa-B-homo-5α-cholestan-6-one is prepared. 제2항에 있어서, 2α,3α-이소프로필리덴디옥시-22S,23S- 디하이드록시-24-에틸-7-옥사-B-호모-5α-콜레스탄-6-온을 제조하는 방법.The method of claim 2, wherein 2α, 3α-isopropylidenedioxy-22S, 23S-dihydroxy-24-ethyl-7-oxa-B-homo-5α-cholestan-6-one is prepared. 제2항에 있어서, 2α,3α-이소프로필리덴디옥시-22S,23S - 디하이드록시-24-에틸-7-옥사-B-호모-5α-콜레스탄-6-온을 제조하는 방법.The process of claim 2, wherein 2α, 3α-isopropylidenedioxy-22S, 23S-dihydroxy-24-ethyl-7-oxa-B-homo-5α-cholestan-6-one is prepared. 제2항에 있어서, 2β,3β-이소프로필리덴디옥시-22S,23S - 디하이드록시-24-에틸-7-옥사-B-호모-5α-콜레스탄-6-온을 제조하는 방법.The process of claim 2, wherein 2β, 3β-isopropylidenedioxy-22S, 23S-dihydroxy-24-ethyl-7-oxa-B-homo-5α-cholestan-6-one is prepared. 제2항에 있어서, 2α,3α-(1-에톡시-에틸리덴디옥시)-22S,23S - 디하이드록시-24-에틸-7-옥사-B-호모-5α-콜레스탄-6-온을 제조하는 방법.The method of claim 2, wherein 2α, 3α- (1-ethoxy-ethylidenedioxy) -22S, 23S-dihydroxy-24-ethyl-7-oxa-B-homo-5α-cholestan-6-one How to prepare. 제2항에 있어서, 2α,3α-(1-에톡시-에틸리덴디옥시)-22S,23S - 디하이드록시-24-에틸-7-옥사-B-호모-5α-콜레스탄-6-온을 제조하는 방법.The method of claim 2, wherein 2α, 3α- (1-ethoxy-ethylidenedioxy) -22S, 23S-dihydroxy-24-ethyl-7-oxa-B-homo-5α-cholestan-6-one How to prepare. 제2항에 있어서, 2α,3α-(1-메톡시-메틸리덴디옥시)-22R,23R - 디하이드록시-24-에틸-7-옥사-B-호모-5α-콜레스탄-6-온을 제조하는 방법.The compound of claim 2, wherein 2α, 3α- (1-methoxy-methylidenedioxy) -22R, 23R-dihydroxy-24-ethyl-7-oxa-B-homo-5α-cholestan-6-one How to prepare. 제2항에 있어서, 2β,3β-(1-에톡시-에틸리덴디옥시)-22S,23S - 디하이드록시-24-에틸-7-옥사-B-호모-5α-콜레스탄-6-온을 제조하는 방법.The method of claim 2, wherein the 2β, 3β- (1-ethoxy-ethylidenedioxy) -22S, 23S-dihydroxy-24-ethyl-7-oxa-B-homo-5α-cholestan-6-one How to prepare. 제2항에 있어서, 2α,3α-(1-메틸-1-페닐-메틸렌디옥시)-22S,23S - 디하이드록시-24-에틸-7-옥사-B-호모-5α-콜레스탄-6-온을 제조하는 방법.The method of claim 2, wherein 2α, 3α- (1-methyl-1-phenyl-methylenedioxy) -22S, 23S-dihydroxy-24-ethyl-7-oxa-B-homo-5α-cholestane-6 A method of preparing the ion. 제2항에 있어서, 2α,3α-(1-메틸-1-페닐-메틸렌디옥시)-22S,23S - 디하이드록시-24-에틸-6-옥사-B-호모-5α-콜레스탄-7-온을 제조하는 방법.The method of claim 2, wherein 2α, 3α- (1-methyl-1-phenyl-methylenedioxy) -22S, 23S-dihydroxy-24-ethyl-6-oxa-B-homo-5α-cholestane-7 A method of preparing the ion. 제2항에 있어서, 2α,3α-카보닐디옥시-22S,23S -디하이드록시-24-에틸-6-옥사-B-호모-5α-콜레스탄-7-온을 제조하는 방법.The process of claim 2, wherein 2α, 3α-carbonyldioxy-22S, 23S-dihydroxy-24-ethyl-6-oxa-B-homo-5α-cholestan-7-one is prepared. 제2항에 있어서, 2α,3α-카보닐디옥시-22R,23R -디하이드록시-24-에틸-6-옥사-B-호모-5α-콜레스탄-7-온을 제조하는 방법.The process of claim 2, wherein 2α, 3α-carbonyldioxy-22R, 23R-dihydroxy-24-ethyl-6-oxa-B-homo-5α-cholestan-7-one is prepared. 제2항에 있어서, 2α,3α-벤질리덴디옥시-22S,23S -디하이드록시-24-에틸-6-옥사-B-호모-5α-콜레스탄-7-온을 제조하는 방법.The method of claim 2, wherein 2α, 3α-benzylidenedioxy-22S, 23S-dihydroxy-24-ethyl-6-oxa-B-homo-5α-cholestan-7-one is prepared. 제2항에 있어서, 2α,3α-벤질리덴디옥시-22R,23R -디하이드록시-24-에틸-7-옥사-B-호모-5α-콜레스탄-6-온을 제조하는 방법.The method of claim 2, wherein 2α, 3α-benzylidenedioxy-22R, 23R-dihydroxy-24-ethyl-7-oxa-B-homo-5α-cholestan-6-one is prepared. 제2항에 있어서, 2α,3α-벤질리덴디옥시-22S,23S -디하이드록시-24-에틸-7-옥사-B-호모-5α-콜레스탄-6-온을 제조하는 방법.The process of claim 2, wherein 2α, 3α-benzylidenedioxy-22S, 23S-dihydroxy-24-ethyl-7-oxa-B-homo-5α-cholestan-6-one is prepared. 제1항에 있어서, 2α,3α-디헥사노일옥시-22S,23S -디하이드록시-24-에틸-7-옥사-B-호모-5α-콜레스탄-6-온을 제조하는 방법.The method of claim 1, wherein 2α, 3α-dihexanoyloxy-22S, 23S-dihydroxy-24-ethyl-7-oxa-B-homo-5α-cholestan-6-one is prepared. 제1항에 있어서, 2α,22S,-디헥사노일옥시-3α,23S-디하이드록시-24-에틸-7-옥사-B-호모-5α-콜레스탄-6-온을 제조하는 방법.The method of claim 1, wherein 2α, 22S, -dihexanoyloxy-3α, 23S-dihydroxy-24-ethyl-7-oxa-B-homo-5α-cholestan-6-one is prepared. 제1항에 있어서,2α,3α-디아세톡시-22S,23S -디하이드록시-24-에틸-7-옥사-B-호모-5α-콜레스탄-6-온을 제조하는 방법.The method of claim 1, wherein 2α, 3α-diacetoxy-22S, 23S-dihydroxy-24-ethyl-7-oxa-B-homo-5α-cholestan-6-one is prepared. 제1항에 있어서,2α,3α-디아세톡시-22S,23S -디하이드록시-24-에틸-6-옥사-B-호모-5α-콜레스탄-7-온을 제조하는 방법.The method of claim 1, wherein 2α, 3α-diacetoxy-22S, 23S-dihydroxy-24-ethyl-6-oxa-B-homo-5α-cholestan-7-one is prepared. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019830004316A 1982-09-15 1983-09-14 Method for preparing 28-methyl-brasinosteroid derivatives KR840005737A (en)

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