bis(2-trimethylsilylethyl) (2S)-2-(phenylmethoxycarbonylamino)butanedioate | 1159497-10-5

• 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: bis(2-trimethylsilylethyl) (2S)-2-(phenylmethoxycarbonylamino)butanedioate
• CAS: 1159497-10-5
• 化学式: C₂₂H₃₇NO₆Si₂
• 分子量: 467.71
• InChiKey: ZCZWRENVRTUCKV-IBGZPJMESA-N

物化性质

• 沸点：
  527.4±50.0 °C(predicted)
• 密度：
  1.052±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 重原子数：
  31
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  bis(2-trimethylsilylethyl) (2S)-2-(phenylmethoxycarbonylamino)butanedioate 在 Alcalase-cross-linked-enzyme-aggregates 作用下， 以 叔丁醇 为溶剂， 反应 16.0h， 以85%的产率得到Cbz-Asp-(OTMSE)-OH
  参考文献：
  名称：

  A versatile and selective chemo-enzymatic synthesis of β-protected aspartic and γ-protected glutamic acid derivatives

  摘要：

  Two versatile, high yielding, and efficient chemo-enzymatic methods for the synthesis of beta-protected Asp and gamma-protected Glu derivatives using Alcalase are described. The first method is based on the alpha-selective enzymatic hydrolysis of symmetrical aspartyl and glutamyl diesters. The second method involving mixed diesters comprises a three-step protocol using (i) alpha-selective enzymatic methyl-esterification, (ii) chemical beta-esterification, and finally (iii) alpha-selective enzymatic methyl ester hydrolysis. The yields of the purified beta- and gamma-esters range from 77% to 91%. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.03.130
• 作为产物：
  描述：

  2-(三甲硅基)乙醇 、 N-CBZ-L-天冬氨酸 在 N-羟基-7-氮杂苯并三氮唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 bis(2-trimethylsilylethyl) (2S)-2-(phenylmethoxycarbonylamino)butanedioate
  参考文献：
  名称：

  A versatile and selective chemo-enzymatic synthesis of β-protected aspartic and γ-protected glutamic acid derivatives

  摘要：

  Two versatile, high yielding, and efficient chemo-enzymatic methods for the synthesis of beta-protected Asp and gamma-protected Glu derivatives using Alcalase are described. The first method is based on the alpha-selective enzymatic hydrolysis of symmetrical aspartyl and glutamyl diesters. The second method involving mixed diesters comprises a three-step protocol using (i) alpha-selective enzymatic methyl-esterification, (ii) chemical beta-esterification, and finally (iii) alpha-selective enzymatic methyl ester hydrolysis. The yields of the purified beta- and gamma-esters range from 77% to 91%. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.03.130