prop-2-enyl 2-[(3S,10R,13E,16S)-10-[(3-chloro-4-methoxyphenyl)methyl]-16-[(1S)-1-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]ethyl]-6,6-dimethyl-2,5,9,12-tetraoxo-1,4-dioxa-8,11-diazacyclohexadec-13-en-3-yl]acetate | 1248798-82-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: prop-2-enyl 2-[(3S,10R,13E,16S)-10-[(3-chloro-4-methoxyphenyl)methyl]-16-[(1S)-1-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]ethyl]-6,6-dimethyl-2,5,9,12-tetraoxo-1,4-dioxa-8,11-diazacyclohexadec-13-en-3-yl]acetate
• CAS: 1248798-82-4
• 化学式: C₄₀H₄₉ClN₂O₁₁
• 分子量: 769.289
• InChiKey: PRQYLRLQCZGYQB-RDWXGGRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  54
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  165
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  prop-2-enyl 2-[(3S,10R,13E,16S)-10-[(3-chloro-4-methoxyphenyl)methyl]-16-[(1S)-1-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]ethyl]-6,6-dimethyl-2,5,9,12-tetraoxo-1,4-dioxa-8,11-diazacyclohexadec-13-en-3-yl]acetate 在 水 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成
  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：

  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 在 水 、 三苯基膦 、 2-羟基吡啶 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.92h， 以32%的产率得到prop-2-enyl 2-[(3S,10R,13E,16S)-10-[(3-chloro-4-methoxyphenyl)methyl]-16-[(1S)-1-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]ethyl]-6,6-dimethyl-2,5,9,12-tetraoxo-1,4-dioxa-8,11-diazacyclohexadec-13-en-3-yl]acetate
  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