(3S,4S)-Methyl 4-<(tert-Butoxycarbonyl)amino>-3,5-bis<(tert-butyldimethylsilyl)oxy>pentanoate | 130096-79-6

• 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: (3S,4S)-Methyl 4-<(tert-Butoxycarbonyl)amino>-3,5-bis<(tert-butyldimethylsilyl)oxy>pentanoate
• 英文别名: methyl (3S,4S)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-4-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate
• CAS: 130096-79-6
• 化学式: C₂₃H₄₉NO₆Si₂
• 分子量: 491.816
• InChiKey: VSKSENDXIYBBFZ-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.86
• 重原子数：
  32
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S,4S)-Methyl 4-<(tert-Butoxycarbonyl)amino>-3,5-bis<(tert-butyldimethylsilyl)oxy>pentanoate 在 二异丁基氢化铝 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 19.5h， 生成 (5S,6S)-Methyl 6-<(tert-Butoxycarbonyl)amino>-5,7-bis<(tert-butyldimethylsilyl)oxy>-2-heptenoate
  参考文献：
  名称：

  Asymmetric intramolecular amidation of N-(tert-butoxycarbonyl)-3-hydroxy-4-pentenylamine. A new entry to chiral building blocks for the synthesis of biologically active nitrogen-containing compounds

  摘要：

  Sharpless reaction of racemic N-(tert-butoxycarbonyl)-3-hydroxy-4-pentenylamine (1) leads to both an asymmetric kinetic resolution to provide optically active 1, which was subsequently used for intramolecular amidomercuration, and asymmetric epoxidation followed by concomitant cyclization into optically active cis-3-hydroxy-2-(hydroxymethyl)pyrrolidine (3). Optically active 1 and 3 have been expediently used as chiral building blocks in the asymmetric synthesis of several biologically active natural products.

  DOI：

  10.1021/jo00001a045
• 作为产物：
  描述：

  (2R,3S)-1-(tert-Butoxycarbonyl)-2-(bromomercuri)-3-hydroxypyrrolidine 在 4-二甲氨基吡啶 咪唑 、 ruthenium(IV) oxide 、 sodium periodate 作用下， 以 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 (3S,4S)-Methyl 4-<(tert-Butoxycarbonyl)amino>-3,5-bis<(tert-butyldimethylsilyl)oxy>pentanoate
  参考文献：
  名称：

  Asymmetric intramolecular amidation of N-(tert-butoxycarbonyl)-3-hydroxy-4-pentenylamine. A new entry to chiral building blocks for the synthesis of biologically active nitrogen-containing compounds

  摘要：

  Sharpless reaction of racemic N-(tert-butoxycarbonyl)-3-hydroxy-4-pentenylamine (1) leads to both an asymmetric kinetic resolution to provide optically active 1, which was subsequently used for intramolecular amidomercuration, and asymmetric epoxidation followed by concomitant cyclization into optically active cis-3-hydroxy-2-(hydroxymethyl)pyrrolidine (3). Optically active 1 and 3 have been expediently used as chiral building blocks in the asymmetric synthesis of several biologically active natural products.

  DOI：

  10.1021/jo00001a045

文献信息

• TAKAHATA, HIROKI;BANBA, YASUNORI;TAJIMA, MAYUMI;MOMOSE, TAKEFUMI, J. ORG. CHEM., 56,(1991) N, C. 240-245
  作者：TAKAHATA, HIROKI、BANBA, YASUNORI、TAJIMA, MAYUMI、MOMOSE, TAKEFUMI

  DOI：——

  日期：——