[(1R,2S,3S,4R)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-4-((S)-1,2-dihydroxy-ethyl)-cyclobutyl]-carbamic acid tert-butyl ester | 1026902-95-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: [(1R,2S,3S,4R)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-4-((S)-1,2-dihydroxy-ethyl)-cyclobutyl]-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(1R,2S,3S,4R)-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]-4-[(1S)-1,2-dihydroxyethyl]cyclobutyl]carbamate
• CAS: 1026902-95-3
• 化学式: C₂₃H₄₉NO₆Si₂
• 分子量: 491.816
• InChiKey: HNQGFGSULOCEJX-LFDJNIOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  97.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 [(1R,2S,3S,4R)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-4-((S)-1,2-dihydroxy-ethyl)-cyclobutyl]-carbamic acid tert-butyl ester 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 Acetic acid (S)-2-acetoxy-1-[(1R,2R,3S,4S)-2-tert-butoxycarbonylamino-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-cyclobutyl]-ethyl ester
  参考文献：
  名称：

  Role of a Protected Vicinal Diol Controller in Intramolecular [3 + 2] Cycloaddition Reactions of Chiral Acyclic Alkenyl Nitrones: Syntheses of Enantiomerically Pure Tetrasubstituted Cyclobutylamines

  摘要：

  Intramolecular cycloaddition reactions of C-5-chain acyclic alkenyl nitrones such as N-[(2S,3S)-2,3-bis-(tert-butyldimethylsiloxy)-4-pentenylidene]benzylamine N-oxide and its C(5)-substituted derivatives lead to fused isoxazolidines (bicyclo[3.2.0] framework) with very high diastereomeric excess. These isoxazolidines can readily be converted to optically active tetrasubstituted cyclobutylamines.

  DOI：

  10.1021/jo00095a008
• 作为产物：
  描述：

  (4R,6S,7S)-2-Benzyl-4-benzyloxymethyl-6,7-bis-(tert-butyl-dimethyl-silanyloxy)-3-oxa-2-aza-bicyclo[3.2.0]heptane 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 [(1R,2S,3S,4R)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-4-((S)-1,2-dihydroxy-ethyl)-cyclobutyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Role of a Protected Vicinal Diol Controller in Intramolecular [3 + 2] Cycloaddition Reactions of Chiral Acyclic Alkenyl Nitrones: Syntheses of Enantiomerically Pure Tetrasubstituted Cyclobutylamines

  摘要：

  Intramolecular cycloaddition reactions of C-5-chain acyclic alkenyl nitrones such as N-[(2S,3S)-2,3-bis-(tert-butyldimethylsiloxy)-4-pentenylidene]benzylamine N-oxide and its C(5)-substituted derivatives lead to fused isoxazolidines (bicyclo[3.2.0] framework) with very high diastereomeric excess. These isoxazolidines can readily be converted to optically active tetrasubstituted cyclobutylamines.

  DOI：

  10.1021/jo00095a008

文献信息

• Role of a Protected Vicinal Diol Controller in Intramolecular [3 + 2] Cycloaddition Reactions of Chiral Acyclic Alkenyl Nitrones: Syntheses of Enantiomerically Pure Tetrasubstituted Cyclobutylamines
  作者：Seiki Saito、Teruhiko Ishikawa、Toshio Moriwake

  DOI：10.1021/jo00095a008

  日期：1994.8

  Intramolecular cycloaddition reactions of C-5-chain acyclic alkenyl nitrones such as N-[(2S,3S)-2,3-bis-(tert-butyldimethylsiloxy)-4-pentenylidene]benzylamine N-oxide and its C(5)-substituted derivatives lead to fused isoxazolidines (bicyclo[3.2.0] framework) with very high diastereomeric excess. These isoxazolidines can readily be converted to optically active tetrasubstituted cyclobutylamines.