(1S,2S) methyl 2-([tert-butyl(diphenyl)silyloxy]methyl)-1-(4-methoxybenzyloxy)-3-cyclopentene-1-carboxylate | 851626-51-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2S) methyl 2-([tert-butyl(diphenyl)silyloxy]methyl)-1-(4-methoxybenzyloxy)-3-cyclopentene-1-carboxylate
• 英文别名: (1S,2S)-2-[(tert-butyldiphenylsilanyloxy)methyl]-1-(4-methoxybenzyloxy)cyclopent-3-enecarboxylic acid methyl ester；methyl (1S,2S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-1-[(4-methoxyphenyl)methoxy]cyclopent-3-ene-1-carboxylate
• CAS: 851626-51-2
• 化学式: C₃₂H₃₈O₅Si
• 分子量: 530.736
• InChiKey: UREURCKLTYSRIV-IEWVHIKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.28
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,2S) methyl 2-([tert-butyl(diphenyl)silyloxy]methyl)-1-(4-methoxybenzyloxy)-3-cyclopentene-1-carboxylate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以64%的产率得到(1S,2S)-2-(hydroxymethyl)-1-(4-methoxybenzyloxy)cyclopent-3-enecarboxylic acid methyl ester
  参考文献：
  名称：

  Directed Diastereoselectivity in the Asymmetric Claisen/Metathesis Reaction Sequence

  摘要：

  The Claisen/metathesis sequence is a versatile synthetic tool for the synthesis of quaternary hydroxy and amino acid carbocycles. By correctly choosing both the configuration of the allylic alcohol and the double bond geometry, specific access to any one of four possible stereoisomers is possible in good yield and excellent diastereoselectivity. The enantiomerically pure allylic alcohols are easily obtained by addition of terminal alkynes to aldehydes. Controlled reduction of the triple bond then gives the desired double bond geometry.

  DOI：

  10.1021/jo800496h
• 作为产物：
  描述：

  (2S,3S)-2-Allyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-pent-4-enoic acid methyl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以70%的产率得到(1S,2S) methyl 2-([tert-butyl(diphenyl)silyloxy]methyl)-1-(4-methoxybenzyloxy)-3-cyclopentene-1-carboxylate
  参考文献：
  名称：

  Highly enantioselective sequential Claisen–Ireland/metathesis: synthesis of cycloalkenes bearing two contiguous highly functionalized asymmetric centres

  摘要：

  A sequence of two reactions, consisting of a highly stereoselective silylated ketene acetal Claisen-Ireland rearrangement followed by a ring closing metathesis, gave a stereocontrolled access to various carbocycles. (C) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2004.12.029

文献信息

• Highly enantioselective sequential Claisen–Ireland/metathesis: synthesis of cycloalkenes bearing two contiguous highly functionalized asymmetric centres
  作者：Antoine Français、Olivier Bedel、Willy Picoul、Abdelkrim Meddour、Jacques Courtieu、Arnaud Haudrechy

  DOI：10.1016/j.tetasy.2004.12.029

  日期：2005.3

  A sequence of two reactions, consisting of a highly stereoselective silylated ketene acetal Claisen-Ireland rearrangement followed by a ring closing metathesis, gave a stereocontrolled access to various carbocycles. (C) 2005 Published by Elsevier Ltd.
• Directed Diastereoselectivity in the Asymmetric Claisen/Metathesis Reaction Sequence
  作者：Nicolas P. Probst、Arnaud Haudrechy、Karen Plé

  DOI：10.1021/jo800496h

  日期：2008.6.1

  The Claisen/metathesis sequence is a versatile synthetic tool for the synthesis of quaternary hydroxy and amino acid carbocycles. By correctly choosing both the configuration of the allylic alcohol and the double bond geometry, specific access to any one of four possible stereoisomers is possible in good yield and excellent diastereoselectivity. The enantiomerically pure allylic alcohols are easily obtained by addition of terminal alkynes to aldehydes. Controlled reduction of the triple bond then gives the desired double bond geometry.