benzyl N-[(1S,2S)-2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)-3-trimethylsilylpropyl]carbamate | 335170-39-3

• 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: benzyl N-[(1S,2S)-2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)-3-trimethylsilylpropyl]carbamate
• CAS: 335170-39-3
• 化学式: C₂₀H₃₁NO₆Si
• 分子量: 409.555
• InChiKey: HTTBXFPQJUIYBG-WSCVDHEUSA-N

物化性质

• 沸点：
  531.8±50.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl N-[(1S,2S)-2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)-3-trimethylsilylpropyl]carbamate 在 盐酸 作用下， 生成 L-乙烯基甘氨酸
  参考文献：
  名称：

  Synthesis of enantiomerically enriched β,γ-unsaturated-α-amino acids

  摘要：

  A variety of enantiomerically enriched beta,gamma -unsaturated-alpha -amino acids are synthesized by olefination of a Cbz-protected serine aldehyde equivalent, readily prepared from serine. A cyclic ortho ester protecting group is employed to minimize racemization. The deprotected amino acids are obtained in good yield, ranging from 70-95% ee, with double-bond geometry determined by the type of Wittig reagent used. Isotopically labeled side chains are readily introduced by this procedure, and free gamma-C-13-vinylglycine was prepared in 44% yield from the protected serine aldehyde synthon. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01146-7
• 作为产物：
  描述：

  3-甲基-3-羟甲基氧杂环丁烷 在 草酰氯 、 三氟化硼乙醚 、 二甲基亚砜 、 sodium iodide 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 63.5h， 生成 benzyl N-[(1S,2S)-2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)-3-trimethylsilylpropyl]carbamate
  参考文献：
  名称：

  Synthesis of enantiomerically enriched β,γ-unsaturated-α-amino acids

  摘要：

  A variety of enantiomerically enriched beta,gamma -unsaturated-alpha -amino acids are synthesized by olefination of a Cbz-protected serine aldehyde equivalent, readily prepared from serine. A cyclic ortho ester protecting group is employed to minimize racemization. The deprotected amino acids are obtained in good yield, ranging from 70-95% ee, with double-bond geometry determined by the type of Wittig reagent used. Isotopically labeled side chains are readily introduced by this procedure, and free gamma-C-13-vinylglycine was prepared in 44% yield from the protected serine aldehyde synthon. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01146-7

文献信息

• Synthesis of enantiomerically enriched β,γ-unsaturated-α-amino acids
  作者：Nicholas G.W Rose、Mark A Blaskovich、Alex Wong、Gilles A Lajoie

  DOI：10.1016/s0040-4020(00)01146-7

  日期：2001.2

  A variety of enantiomerically enriched beta,gamma -unsaturated-alpha -amino acids are synthesized by olefination of a Cbz-protected serine aldehyde equivalent, readily prepared from serine. A cyclic ortho ester protecting group is employed to minimize racemization. The deprotected amino acids are obtained in good yield, ranging from 70-95% ee, with double-bond geometry determined by the type of Wittig reagent used. Isotopically labeled side chains are readily introduced by this procedure, and free gamma-C-13-vinylglycine was prepared in 44% yield from the protected serine aldehyde synthon. (C) 2001 Elsevier Science Ltd. All rights reserved.