(S)-4-(allyloxy)-2-(3-azido-2,2-dimethylpropanoyloxy)-4-oxobutanoic acid | 1248798-79-9

• 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: (S)-4-(allyloxy)-2-(3-azido-2,2-dimethylpropanoyloxy)-4-oxobutanoic acid
• 英文别名: (2S)-2-(3-azido-2,2-dimethylpropanoyl)oxy-4-oxo-4-prop-2-enoxybutanoic acid
• CAS: 1248798-79-9
• 化学式: C₁₂H₁₇N₃O₆
• 分子量: 299.283
• InChiKey: SXCOJNBQFGUNRG-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-4-(allyloxy)-2-(3-azido-2,2-dimethylpropanoyloxy)-4-oxobutanoic acid 、 (R)-3-(3-Chloro-4-methoxy-phenyl)-2-[(E)-(5S,6S)-6-((4R,5R)-2,2-dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-5-hydroxy-hept-2-enoylamino]-propionic acid 2,2,2-trichloro-ethyl ester 在 4-二甲氨基吡啶 、 2,4,6-三氯苯甲酰氯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.25h， 以81%的产率得到1-O-[(E,2S,3S)-7-[[(2R)-3-(3-chloro-4-methoxyphenyl)-1-oxo-1-(2,2,2-trichloroethoxy)propan-2-yl]amino]-2-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-7-oxohept-5-en-3-yl] 4-O-prop-2-enyl (2S)-2-(3-azido-2,2-dimethylpropanoyl)oxybutanedioate
  参考文献：
  名称：

  Approaches for the Synthesis of Functionalized Cryptophycins

  摘要：

  The first syntheses of bioactive cryptophycins functionalized at unit ID were accomplished ina one-pot Staudinger reduction/cyclization step An a/ado precursor for the lower part of the backbone was introduced to minimize protective group chemistry and enable a very convenient synthesis of cryptophycin-52 and unit D eryptophycin analogues containing an ester or a free carboxylic acid for bioconjugations Both new cryptophycin derivatives show high biological activity in cytotoxicity assays

  DOI：

  10.1021/jo101563s
• 作为产物：
  描述：

  4-allyl 1-tert-butyl (S)-2-(3-azido-2,2-dimethylpropanoyloxy)succinate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以100%的产率得到(S)-4-(allyloxy)-2-(3-azido-2,2-dimethylpropanoyloxy)-4-oxobutanoic acid
  参考文献：
  名称：

  Approaches for the Synthesis of Functionalized Cryptophycins

  摘要：

  The first syntheses of bioactive cryptophycins functionalized at unit ID were accomplished ina one-pot Staudinger reduction/cyclization step An a/ado precursor for the lower part of the backbone was introduced to minimize protective group chemistry and enable a very convenient synthesis of cryptophycin-52 and unit D eryptophycin analogues containing an ester or a free carboxylic acid for bioconjugations Both new cryptophycin derivatives show high biological activity in cytotoxicity assays

  DOI：

  10.1021/jo101563s

文献信息

• Approaches for the Synthesis of Functionalized Cryptophycins
  作者：Benedikt Sammet、Tobias Bogner、Markus Nahrwold、Christine Weiss、Norbert Sewald

  DOI：10.1021/jo101563s

  日期：2010.10.15

  The first syntheses of bioactive cryptophycins functionalized at unit ID were accomplished ina one-pot Staudinger reduction/cyclization step An a/ado precursor for the lower part of the backbone was introduced to minimize protective group chemistry and enable a very convenient synthesis of cryptophycin-52 and unit D eryptophycin analogues containing an ester or a free carboxylic acid for bioconjugations Both new cryptophycin derivatives show high biological activity in cytotoxicity assays