5-<(5S)-<(Benzyloxycarbonyl)amino>methyl>-2,2-bis(trifluoromethyl)-1,3-dioxolan-4-one | 170997-04-3

• 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: 5-<(5S)-<(Benzyloxycarbonyl)amino>methyl>-2,2-bis(trifluoromethyl)-1,3-dioxolan-4-one
• 英文别名: benzyl N-[[(4S)-5-oxo-2,2-bis(trifluoromethyl)-1,3-dioxolan-4-yl]methyl]carbamate
• CAS: 170997-04-3
• 化学式: C₁₄H₁₁F₆NO₅
• 分子量: 387.235
• InChiKey: GVSZKJOCCMLVFI-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  L-苯基丙氨酸叔丁酯 、 5-<(5S)-<(Benzyloxycarbonyl)amino>methyl>-2,2-bis(trifluoromethyl)-1,3-dioxolan-4-one 以 乙醚 为溶剂， 以30%的产率得到phenylalanine tert-butyl ester
  参考文献：
  名称：

  New Efficient Strategy for the Incorporation of (S)-Isoserine into Peptides

  摘要：

  A new efficient synthesis of (S)-isoserine derivatives from (S)-malic acid using hexafluoroacetone as protecting and activating reagent is described. Via this route (S)-isoserine is obtained as mono- and diactivated species suitable for the incorporation of isoserine into the N- and C-terminal positions of peptides.

  DOI：

  10.1021/jo00128a042
• 作为产物：
  描述：

  [(5S)-2,2-Bis(trifluoromethyl)-4-oxo-1,3-dioxolan-5-yl] acetic acid 在 氯化亚砜 、 叠氮基三甲基硅烷 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 46.0h， 生成 5-<(5S)-<(Benzyloxycarbonyl)amino>methyl>-2,2-bis(trifluoromethyl)-1,3-dioxolan-4-one
  参考文献：
  名称：

  New Efficient Strategy for the Incorporation of (S)-Isoserine into Peptides

  摘要：

  A new efficient synthesis of (S)-isoserine derivatives from (S)-malic acid using hexafluoroacetone as protecting and activating reagent is described. Via this route (S)-isoserine is obtained as mono- and diactivated species suitable for the incorporation of isoserine into the N- and C-terminal positions of peptides.

  DOI：

  10.1021/jo00128a042

文献信息

• New Efficient Strategy for the Incorporation of (S)-Isoserine into Peptides
  作者：Klaus Burger、Elisabeth Windeisen、Raul Pires

  DOI：10.1021/jo00128a042

  日期：1995.11

  A new efficient synthesis of (S)-isoserine derivatives from (S)-malic acid using hexafluoroacetone as protecting and activating reagent is described. Via this route (S)-isoserine is obtained as mono- and diactivated species suitable for the incorporation of isoserine into the N- and C-terminal positions of peptides.