<(5S)-2,2-Bis(trifluoromethyl)-4-oxo-1,3-dioxolan-5-yl>methyl isocyanate | 172540-29-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: <(5S)-2,2-Bis(trifluoromethyl)-4-oxo-1,3-dioxolan-5-yl>methyl isocyanate
• 英文别名: [(5S)-2,2-bis(trifluoromethyl)-4-oxo-1,3-dioxolan-5-yl]methyl isocyanate；[[2,2-Bis(trifluoromethyl)-5-oxo-1,3-dioxolan-4beta-yl]methyl] isocyanate；(5S)-5-(isocyanatomethyl)-2,2-bis(trifluoromethyl)-1,3-dioxolan-4-one
• CAS: 172540-29-3
• 化学式: C₇H₃F₆NO₄
• 分子量: 279.096
• InChiKey: OFIYRPSTYBUQAG-VKHMYHEASA-N

物化性质

• 沸点：
  247.1±35.0 °C(Predicted)
• 密度：
  1.71±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  65
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  苄氧羰基-L-丙氨酸 、 <(5S)-2,2-Bis(trifluoromethyl)-4-oxo-1,3-dioxolan-5-yl>methyl isocyanate 以 甲苯 为溶剂， 反应 18.0h， 以87%的产率得到N-(Benzyloxycarbonyl)alanine-N'-<<(5S)-2,2-bis(trifluoromethyl)-4-oxo-1,3-dioxolan-5-yl>methyl>amide
  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 甲苯 为溶剂， 反应 6.0h， 生成 <(5S)-2,2-Bis(trifluoromethyl)-4-oxo-1,3-dioxolan-5-yl>methyl isocyanate
  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

• On Penicillin-Binding Protein 1b Affinity-Labeling Reagents
  作者：Daniela Volke、Mohammed Daghish、Lothar Hennig、Matthias Findeisen、Sabine Giesa、Ramona Oehme、Peter Welzel

  DOI：10.1002/hlca.200390346

  日期：2003.12

  orthogonally. To three of the labels, moenomycin was conjugated with the aim to provide tools for the identification of the moenomycin binding site within the transglycosylase domain of the enzyme PBP 1b. Some preliminary photoaffinity-labeling experiments were carried out.

  报道了一些3-芳基-3-（三氟甲基）3 H-二嗪和基于二苯甲酮的光亲和标记的合成。光不稳定基团结合到支架上，该支架也容纳指示剂单元（生物素）和生物活性配体可以正交连接的官能团。为了提供三个工具，用于鉴定酶PBP 1b的转糖基化酶结构域内的moenomycin结合位点，将moenomycin与三个标记物进行了缀合。进行了一些初步的光亲和标记实验。
• New types of glycoconjugates: O-glycosylated, N-glycosylated and O-,N-diglycosylated isoserine derivatives
  作者：Christoph Böttcher、Klaus Burger

  DOI：10.1016/s0040-4039(03)00896-7

  日期：2003.5

  Starting from hexafluoroacetone-protected malic acid O-glycosylated, N-glycosylated and O-,N-diglycosylated (S)-isoserine derivatives have been synthesized. The new compounds represent glycosylated β-alanine surrogates, i.a. suitable for β-peptide modification.

  从六氟丙酮保护苹果酸起始ø -glycosylated，Ñ -glycosylated和ø - ，Ñ -diglycosylated（小号）-isoserine衍生物已被合成。新化合物代表糖基化的β-丙氨酸替代物，其适用于β-肽修饰。
• 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.
• 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.