(1S,2R) methyl 1-[(tert-butoxycarbonyl)amino]-2-([tert-butyl(diphenyl)silyloxy]methyl)-3-cyclopentene-1-carboxylate | 851626-56-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1S,2R) methyl 1-[(tert-butoxycarbonyl)amino]-2-([tert-butyl(diphenyl)silyloxy]methyl)-3-cyclopentene-1-carboxylate
• 英文别名: (1S,2R)-1-(tert-butoxycarbonylamino)-2-[(tert-butyldiphenylsilanyloxy)methyl]cyclopent-3-enecarboxylic acid methyl ester；methyl (1S,2R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopent-3-ene-1-carboxylate
• CAS: 851626-56-7
• 化学式: C₂₉H₃₉NO₅Si
• 分子量: 509.718
• InChiKey: UAOCMKBPNKSZQR-ZTOMLWHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.58
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,2R) methyl 1-[(tert-butoxycarbonyl)amino]-2-([tert-butyl(diphenyl)silyloxy]methyl)-3-cyclopentene-1-carboxylate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以82%的产率得到(1S,2R)-1-(tert-butoxycarbonylamino)-2-(hydroxymethyl)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,3R)-2-Allyl-2-tert-butoxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-4-enoic acid 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， 生成 (1S,2R) methyl 1-[(tert-butoxycarbonyl)amino]-2-([tert-butyl(diphenyl)silyloxy]methyl)-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