(4R,5R)-3-(5-Methyl-2-oxo-[1,3]dioxolan-4-yl)-acrylic acid ethyl ester | 430425-34-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (4R,5R)-3-(5-Methyl-2-oxo-[1,3]dioxolan-4-yl)-acrylic acid ethyl ester
• 英文别名: ethyl (E)-3-[(4R,5R)-5-methyl-2-oxo-1,3-dioxolan-4-yl]prop-2-enoate
• CAS: 430425-34-6
• 化学式: C₉H₁₂O₅
• 分子量: 200.191
• InChiKey: SWEGBYCFHBQPIG-XIMOZBJHSA-N

物化性质

• 沸点：
  339.3±35.0 °C(Predicted)
• 密度：
  1.253±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R,5R)-3-(5-Methyl-2-oxo-[1,3]dioxolan-4-yl)-acrylic acid ethyl ester 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 吡啶 、 4-二甲氨基吡啶 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 lithium hydroxide 、 甲酸 、 Dowex 50W-8H⁽¹⁺⁾ resin 、 trichlorobenzoyl chloride 、 四丁基氟化铵 、 4-(dimethylamino)pyridine hydrochloride 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三苯基膦 、 苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 123.0h， 生成 cis-colletol
  参考文献：
  名称：

  Enantioselective Syntheses of Colletodiol, Colletol, and Grahamimycin A

  摘要：

  [GRAPHICS]The enantioselective synthesis of colletodiol has been achieved in 11 steps from methyl 1,3,5-octatrienoate and 16 total steps from both ethyl sorbate and methyl 1,3,5-octatrienoate. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form a 5-hydroxy-1-enoate and an 7-hydroxy-1,3-dienoate. These esters were further functionalized, coupled, and macrolactonized to provide colletodiol after deprotection. Grahamimycin A and colletol were synthesized in one and two steps, respectively, from colletodiol.

  DOI：

  10.1021/ol0269502
• 作为产物：
  描述：

  山梨酸乙酯 在 吡啶 、 甲基磺酰胺 、 AD-mix-β 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 26.0h， 生成 (4R,5R)-3-(5-Methyl-2-oxo-[1,3]dioxolan-4-yl)-acrylic acid ethyl ester
  参考文献：
  名称：

  一条通向2,4,6-苯氧基-4-氨基己糖的通用途径：氨基甲酸酯的碘环化立体异构合成d-乙炔胺及其差向异构体

  摘要：

  通过立体选择性氮官能团的引入和氨基甲酸酯的碘代环化反应，可以完成2,4,6-三苯氧基-4-氨基糖d-维尼西明及其差向异构体3- epi-和4- epi - d-维尼西明的立体选择性合成。这种通用的合成路线始于通过Sharpless不对称二羟基化反应从山梨酸乙酯获得对映体纯的二醇。

  DOI：

  10.1016/j.tet.2017.10.009

文献信息

• An Enantioselective Synthesis of Tarchonanthuslactone
  作者：Sarah D. Garaas、Thomas J. Hunter、George A. O'Doherty

  DOI：10.1021/jo0163400

  日期：2002.4.1

  enantioselective synthesis of tarchonanthuslactone has been achieved in eight steps from ethyl sorbate. The asymmetry of the route was introduced via a Sharpless asymmetric dihydroxylation allowing access to either enantiomer. The synthesis utilizes a palladium-catalyzed reduction and a diastereoselective base-catalyzed acetal formation as the key steps. The pyran ring of tarchonanthuslactone was established

  从山梨酸乙酯通过八个步骤实现了对映体异黄酮内酯的对映选择性合成。路线的不对称性是通过Sharpless不对称二羟基化反应引入的，从而可以进入任一对映体。该合成利用钯催化的还原和非对映选择性碱催化的乙缩醛形成作为关键步骤。土生黄酮内酯的吡喃环通过Still-烯烃化/内酯化序列建立。DCC介导的二氢咖啡酸的附着以19％的总收率完成了土生黄烷内酯的合成。
• De novo asymmetric syntheses of C-4-substituted sugars via an iterative dihydroxylation strategy
  作者：Md. Moinuddin Ahmed、George A. O’Doherty

  DOI：10.1016/j.carres.2006.03.024

  日期：2006.7

  highly efficient route to various C-4 substituted sugar lactones has been developed. The key to the overall transformation is the sequential osmium-catalyzed dihydroxylation reaction of substituted 2,4-dienoates and an allylic substitution at the C-4 position. When the Sharpless AD-mix procedure is used in a matched sense for the second dihydroxylation reaction, it results in an exceedingly diastereo-

  已经开发了一种短且高效的途径来制备各种C-4取代的糖内酯。总体转化的关键是取代的2，4-二烯酸酯的催化的二羟基化反应和C-4位置的烯丙基取代。当将Sharpless AD-mix程序以匹配的方式用于第二个二羟基化反应时，会导致几种C-4取代糖的非对映和对映选择性合成。
• An Enantioselective Synthesis of Benzylidene-Protected <i>syn</i>-3,5-Dihydroxy Carboxylate Esters via Osmium, Palladium, and Base Catalysis
  作者：Thomas J. Hunter、George A. O'Doherty

  DOI：10.1021/ol0156188

  日期：2001.4.1

  [GRAPHICS]The enantioselective syntheses of several protected syn-3,5-dihydroxy carboxylic esters have been achieved from the corresponding achiral 1,3-dieneoates, The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form delta -hydroxy-1-enoates, The resulting delta -hydroxy-1-enoates are subsequently converted into benzylidene-protected 3,5-dihydroxy carboxylic esters in one step, The benzylidene-protected 3,5-dihydroxy carboxylic esters are produced in good overall yields (25% to 51%) and high enantiomeric excesses (80% to >95%).
• A formal, stereoselective synthesis of the natural tetrahydropyran derivative ophiocerin D
  作者：Julián Paños、Juan Murga、Eva Falomir、Miguel Carda、J. Alberto Marco

  DOI：10.1016/j.tetasy.2010.01.013

  日期：2010.3

  A short, formal stereoselective synthesis of the naturally occurring tetrahydropyran derivative ophiocerin D is reported. The four stereocenters of the molecule were created with the aid of two Sharpless asymmetric dihydroxylations. (C) 2010 Elsevier Ltd. All rights reserved.
• A versatile route to 2,4,6-trideoxy-4-aminohexoses: Stereoselective syntheses of d -vicenisamine and its epimers via iodocyclization of carbamate
  作者：Yoshitaka Matsushima、Jun Kino

  DOI：10.1016/j.tet.2017.10.009

  日期：2017.12

  syntheses of the 2,4,6-trideoxy-4-amino sugar d-vicenisamine and its epimers 3-epi- and 4-epi-d-vicenisamine were accomplished via stereoselective nitrogen functional group introduction and iodocyclization of carbamate. This versatile synthetic route started from the enantiomerically pure diol obtained from ethyl sorbate by Sharpless asymmetric dihydroxylation.

  通过立体选择性氮官能团的引入和氨基甲酸酯的碘代环化反应，可以完成2,4,6-三苯氧基-4-氨基糖d-维尼西明及其差向异构体3- epi-和4- epi - d-维尼西明的立体选择性合成。这种通用的合成路线始于通过Sharpless不对称二羟基化反应从山梨酸乙酯获得对映体纯的二醇。