CAS: 37031-29-1; (4R,5R)-Dimethyl 2,2-Dimethyl-1,3-Dioxolane-4,5-Dicarboxylate

该化合物是一种有机二氧醇衍生物,广泛用作非对称合成和制药应用中的关键中间体,其硬性循环结构和立体化学纯度(4R,5R配置)对建造对应式浓缩化合物很有价值.酯功能组提高了有机溶剂的溶性,促进了水解或减少等进一步的转化.二氧醇环在各种反应条件下提供了稳定性,同时在必要时能够有选择地去保护.该化合物在合成具有生物活性分子的合成中特别有用,因为精确的立体控制至关重要.其高纯度和定义明确的立体化学保证了复杂的合成路径的再生性.

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CAS号87-69-4 酒石酸 | CAS号77-76-9 2,2-二甲氧基丙烷 | CAS号608-68-4 L-(+)-酒石酸二甲酯 | CAS号67-64-1 丙酮 | CAS号4744-10-9 丙醛缩二甲醇 | CAS号67-56-1 甲醇 | CAS号87-91-2 L-(+)-酒石酸二乙酯 | CAS号116-11-0 2-甲氧基丙烯 | CAS号186581-53-3 重氮甲烷 | CAS号51064-65-4 1,4-甲苯磺酰基-2,3-异... | CAS号37002-45-2 (-)-1,4-二-O-甲苯磺... | CAS号50622-09-8 (+)-2,3-O-异亚丙基-L-苏糖醇 | CAS号67844-13-7 (4R,5S)-methyl ... | CAS号93379-48-7 (-)-4,5-双[羟基(二苯... | CAS号78086-72-3 (4r,5s)-2,2,5-三... | CAS号73346-74-4 (-)-2,3-O-亚异丙基-... | CAS号119322-88-2 (4S,5S)-4,5-二(氨... | CAS号167282-09-9 [(4R,5R)-5-benz... | CAS号58342-57-7 (+)-反式-4 5-双(碘甲...

合成工艺路线路线简述

    📜L-(+)-酒石酸二甲酯置于草酰氯,三乙胺体系中,用 二氯甲烷,二甲基亚砜 用作溶剂,化学反应 1.0H,反应生成(-)-二甲基-2,3-邻异丙亚基-L-酒石酸酯
    参考文献:Investigation Of Diastereoselective Acyclic α-Alkoxydithioacetal Substitutions Involving Thiacarbenium Intermediates
    标题:Investigation Of Diastereoselective Acyclic α-Alkoxydithioacetal Substitutions Involving Thiacarbenium Intermediates
    摘要:Reported Herein Is An Experimental And Theoretical Study That Elucidates Why Silylated Nucleobase Additions To Acyclic Alpha-Alkoxythiacarbenium Intermediates Proceed With High 1,2-Syn Stereocontrol (Anti-Felkin-Anh),Which Is Opposite To What Would Be Expected With Corresponding Activated Aldehydes. The Acyclic Thioaminals Formed Undergo Intramolecular Cyclizations To Provide Nucleoside Analogues With Anticancer And Antiviral Properties. The Factors Influencing The Selectivity Of The Substitution Reaction Have Been Examined Thoroughly. Halothioether Species Initially Form,Ionize In The Presence (Low Dielectric Media) Or Absence (Higher Dielectric Media) Of The Nucleophile,And React Through S(N)2-Like Transition Structures (Ts A And D),Where The A-Alkoxy Group Is Gauche To The Thioether Moiety. An Important,And Perhaps Counterintuitive,Observation In This Work Was That Calculations Done In The Gas Phase Or Low Dielectric Media (Toluene) Are Essential To Locate The Product-And Rate-Determining Transition Structures (C-N Bond Formation) That Allow The Most Reasonable Prediction Of Selectivity And Isotope Effects For More Polar Solvents (Thf,Mecn). The Triangle Triangle G +/-(G(Tsa)-(Tsd)) Obtained In Silico Are Consistent With The Preferential Formation Of 1,2-Syn Product And With The Trends Of Stereocontrol Displayed By 2,3-Anti And 2,3-Syn Alpha,Beta-Bis-Alkoxydithioacetals.
    Doi:10.1021/jo502181A

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    主要参考文献

    参考标题:The Detosylation Of Chiral 1,2-Bis(Tosylamides)
    作者:Jayden J. Gaston,Andrew J. Tague,Jamie E. Smyth,Nicholas M. Butler,Anthony C. Willis,Nico Van Eikema Hommes,Haibo Yu,Timothy Clark,Paul A. Keller |发布日期:2021.7.2
    摘要:The Deprotection Of Chiral 1,2-Bis(Tosylamides) To Their Corresponding 1,2-Diamines Is Mostly Unsuccessful Under Standard Conditions. In A New Methodology, The Use Of Mg/meoh With Sufficient Steric Additions Allows The Facile Synthesis Of 1,2-Diamines In 78-98% Yields. These Results Are Rationalized Using Density Functional Theory And The Examination Of Inner And Outer-Sphere Reduction Mechanisms.
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