CAS: 105560-93-8; Methyl (2R,3S)-3-(4-Methoxyphenyl)Oxirane-2-Carboxylate

该化合物是一种在非对称合成和制药中间体中有很大用途的手性环氧酯化合物,其立体特性(2R,3S)配置和环氧功能组使其成为构建复杂的分子框架,特别是生物活性化合物合成中复杂的分子框架的宝贵基石.四甲基苯基组的存在增强了其在核循环开关反应中的再活动性,使得能够精确的立体化学控制.该化合物通常用于制备精细化学品和皮环,其高对应纯度和稳定性在受控制的条件下确保了要求合成应用的一贯性能.

结构式图片

相似化合物

42245-42-1 90278-52-7 1823871-42-6

上下游产品

CAS号96125-49-4 2,3-Epoxy-3-(4-... | CAS号71-36-3 正丁醇 | CAS号943-89-5 反-4-甲氧基肉桂酸 | CAS号336113-23-6 (3S)-methyl 2-c... | CAS号3901-07-3 (e)-p-甲氧基肉桂酸甲酯 | CAS号67-56-1 甲醇 | CAS号136597-65-4 (-)-(2R,3S)-sod... | CAS号19310-29-3 3-(4-methoxy-ph... | CAS号42399-40-6 去乙酰地尔硫卓

合成工艺路线路线简述

    📜反式-4-甲氧基肉桂酸置于叔丁基过氧化氢,La-(S)-Binol-Ph3Aso,4 A Molecular Sieve,盐酸-N-乙基-N'-(3-二甲氨基丙基)碳二亚胺体系中,用 四氢呋喃,N,N-二甲基甲酰胺,甲苯 用作溶剂,化学反应 17.0H,反应生成(2R,3S)-(-)-对甲氧苯基缩水甘油酸甲酯
    参考文献:镧系元素-Binol配合物催化α,β-不饱和羧酸咪唑化物和酰胺的不对称环氧化
    标题:镧系元素-Binol配合物催化α,β-不饱和羧酸咪唑化物和酰胺的不对称环氧化
    摘要:研究了α,β-不饱和羧酸咪唑化物和简单酰胺的高度对映选择性催化不对称环氧化反应.在5-10 Mol%的镧系元素-Binol配合物的存在下,反应在高底物普遍性下可顺利进行.特别地,在α,β-不饱和酰胺的情况下,几乎具有完美的对映选择性(> 99%ee).相应的环氧化物已成功转化为多种类型的有用手性化合物,例如α,β-环氧酯,α,β-环氧酰胺,α,β-环氧醛,α,β-环氧β-酮酸酯,α-和β-羟基羰基化合物.进行b3Lyp密度泛函研究以预测底物反应性.
    Doi:10.1016/j.Tet.2003.06.010

    海关参考信息

    专利信息


    专利号:US-6346632-B1
    优先权日:1990-05-17
    标题 :Process for the preparation of intermediates useful for the synthesis for benzothiazepines
    发明人:GHIROTTO LUCA; SERVI STEFANO; FUGANTI CLAUDIO; GENTILE ANGELO; GIORDANO CLAUDIO
    权利人:ZAMBON SPA
    摘要:A process for the preparation of the compounds of formula n (wherein R has the meanings reported in the specification) by enzymatic transesterification of enantiomeric mixtures is described. n These compounds are intermediates useful in the synthesis of Diltiazem.

    专利号:US-5169779-A
    优先权日:1991-02-08
    标 题:Process for the preparation of methyl (-)-(2R,3S)-2,3-epoxy-3-(4-methoxy-phenyl)propionate
    发明人:ZARD LYDIA; TIXIDRE ARLETTE; ROSSEY GUY; WICK ALEXANDER
    权利人:SYNTHELABO
    摘要:A process for the preparation of methyl (-)-(2R,3S)-2,3-epoxy-3-(4-methoxyphenyl)propionate, which comprises subjecting the dextrorotatory (2S,3R) enantiomer, present in a starting mixture containing both the levorotatory (2R,3S and dextrorotatory (2S,3R) enantiomers, to a transesterification reaction, in an anhydrous medium and in the presence of an enzyme which does not affect the levorotatory (2R,3S) enantiomer. The latter is an intermediate for the synthesis of compounds such as Diltiazem.

    专利号:US-6451587-B1
    优先权日:1999-09-29
    标题 :Microbial asymmetric reduction of 2-chloro-1-[-6-(2,5-dimethyl-pyrrol-1-yl)-pyridin-3-yl]-ethanone
    发明人:BURNS MICHAEL P; WONG JOHN W
    权利人:PFIZER
    摘要:The present invention relates to microbial processes for carrying out the asymmetric reduction of a ketone to an alcohol, which comprises: contacting the ketone with a microorganism, or an enzyme reduction system capable of accomplishing the subject reduction comprising an enzyme derived from said microorganism and a co-factor for said enzyme, and incubating the resulting mixture under conditions sufficient to yield more of the desired (R)-enantiomer of the corresponding alcohol than the undesired (S)-enantiomer. The chiral (R)-enantiomer can be used in the synthesis of certain β-adrenergic receptor agonists.

    专利号:DE-4115697-C2
    优先权日:1990-05-17
    标 题 :Process for the preparation of intermediate compounds which can be used in the synthesis of benzothiazepines

    专利号:US-5571704-A
    优先权日:1990-05-17
    标 题 :Process for the preparation of intermediates useful for the synthesis of benzothiazepines

    专利号:NL-9100854-A
    优先权日:1990-05-17
    标 题 :METHOD FOR PREPARING INTERMEDIATES USE FOR THE SYNTHESIS OF BENZODIAZEPINES.

    供应商参考报价(招募中)

    品牌试剂参考报价(招募中)

    📌 第三方产品分析报告

    ✅ COA系统入驻 | 共享模式

    合成参考文献


    摘要:Braverman, S.; Cherkinsky, M., Science of Synthesis Knowledge Updates, (2014) 3, 240.
    摘要:Matsumoto, K.; Katsuki, T.; Arends, I. W. C. E., Science of Synthesis: Stereoselective Synthesis, (2011) 1, 104.
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