5-<(5S)-<(9-Fluorenylmethoxycarbonyl)amino>methyl>-2,2-bis(trifluoromethyl)-1,3-dioxolan-4-one | 170997-03-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 5-<(5S)-<(9-Fluorenylmethoxycarbonyl)amino>methyl>-2,2-bis(trifluoromethyl)-1,3-dioxolan-4-one
• 英文别名: 5-(5S)-[(9-fluorenylmethoxycarbonyl)amino]methyl-2,2-bis(trifluoromethyl)-1,3-dioxolan-4-one；9H-fluoren-9-ylmethyl N-[[(4S)-5-oxo-2,2-bis(trifluoromethyl)-1,3-dioxolan-4-yl]methyl]carbamate
• CAS: 170997-03-2
• 化学式: C₂₁H₁₅F₆NO₅
• 分子量: 475.344
• InChiKey: MOGMKMZNGGTWPS-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  5-<(5S)-<(9-Fluorenylmethoxycarbonyl)amino>methyl>-2,2-bis(trifluoromethyl)-1,3-dioxolan-4-one 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 50.0h， 生成 allyl 3-[(9-fluorenylmethoxycarbonyl)amino]-2-(2S)-[(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)oxy]propionate
  参考文献：
  名称：

  Hexafluoroacetone as a Protecting and Activating Reagent. N- and O-Glycosylation of Isoserine and Isocysteine

  摘要：

  Starting from HFA-protected malic and thiomalic acid a series of O- and N-glycoconjugates suitable for peptide and depsipeptide modification has been synthesized.

  DOI：

  10.1007/s00706-004-0248-9
• 作为产物：
  描述：

  ((5S)-2,2-bis-(trifluoromethyl)-4-oxo-1,3-dioxolan-5-yl)-acetyl chloride 在 叠氮基三甲基硅烷 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 40.0h， 生成 5-<(5S)-<(9-Fluorenylmethoxycarbonyl)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.
• Hexafluoroacetone as a Protecting and Activating Reagent. N- and O-Glycosylation of Isoserine and Isocysteine
  作者：Christoph B�ttcher、Jan Spengler、Lothar Hennig、Fernando Albericio、Klaus Burger

  DOI：10.1007/s00706-004-0248-9

  日期：2005.4

  Starting from HFA-protected malic and thiomalic acid a series of O- and N-glycoconjugates suitable for peptide and depsipeptide modification has been synthesized.