(4E,11E,13E)-(3S,6S,7S,10R)-3,7-Dihydroxy-10-methoxy-4,6,14-trimethyl-9-oxo-15-[3-(2-trimethylsilanyl-ethoxycarbonylamino)-5-(2-trimethylsilanyl-ethoxycarbonyloxy)-phenyl]-pentadeca-4,11,13-trienethioic acid S-(2-acetylamino-ethyl) ester | 875439-84-2

• 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: (4E,11E,13E)-(3S,6S,7S,10R)-3,7-Dihydroxy-10-methoxy-4,6,14-trimethyl-9-oxo-15-[3-(2-trimethylsilanyl-ethoxycarbonylamino)-5-(2-trimethylsilanyl-ethoxycarbonyloxy)-phenyl]-pentadeca-4,11,13-trienethioic acid S-(2-acetylamino-ethyl) ester
• CAS: 875439-84-2
• 化学式: C₄₁H₆₆N₂O₁₁SSi₂
• 分子量: 851.219
• InChiKey: KIQRKKMOUDONKV-VQIXVCERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.54
• 重原子数：
  57.0
• 可旋转键数：
  24.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  186.79
• 氢给体数：
  4.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (4E,11E,13E)-(3S,6S,7S,10R)-3,7-Dihydroxy-10-methoxy-4,6,14-trimethyl-9-oxo-15-[3-(2-trimethylsilanyl-ethoxycarbonylamino)-5-(2-trimethylsilanyl-ethoxycarbonyloxy)-phenyl]-pentadeca-4,11,13-trienethioic acid S-(2-acetylamino-ethyl) ester 在 zinc(II) chloride 作用下， 以 硝基甲烷 为溶剂， 反应 1.0h， 以53%的产率得到S-(2-acetamidoethyl) (3S,4E,6S,7S,10R,11E,13E)-15-(3-amino-5-hydroxyphenyl)-3,7-dihydroxy-10-methoxy-4,6,14-trimethyl-9-oxopentadeca-4,11,13-trienethioate
  参考文献：
  名称：

  Synthesis of the N-Acetylcysteamine Thioester of seco-Proansamitocin

  摘要：

  The enantioselective total synthesis of the N-acetylcysteamine thioester of seco-proansamitocin, a key biosynthetic intermediate of the highly potent antitumor agent ansamitocin, is described, which twice utilizes the Nagao acetate aldol reaction, as well as an indium-mediated alkynylation of a benzyl bromide followed by carboalumination. The key step is a Heck reaction between two terminal alkenes for merging the two major fragments.

  DOI：

  10.1021/ol052588q
• 作为产物：
  描述：

  (4E,11E,13E)-(3S,6S,7S,10R)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-10-methoxy-4,6,14-trimethyl-9-oxo-15-[3-(2-trimethylsilanyl-ethoxycarbonylamino)-5-(2-trimethylsilanyl-ethoxycarbonyloxy)-phenyl]-pentadeca-4,11,13-trienoic acid 在 4-二甲氨基吡啶 、 氟化氢吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 (4E,11E,13E)-(3S,6S,7S,10R)-3,7-Dihydroxy-10-methoxy-4,6,14-trimethyl-9-oxo-15-[3-(2-trimethylsilanyl-ethoxycarbonylamino)-5-(2-trimethylsilanyl-ethoxycarbonyloxy)-phenyl]-pentadeca-4,11,13-trienethioic acid S-(2-acetylamino-ethyl) ester
  参考文献：
  名称：

  Synthesis of the N-Acetylcysteamine Thioester of seco-Proansamitocin

  摘要：

  The enantioselective total synthesis of the N-acetylcysteamine thioester of seco-proansamitocin, a key biosynthetic intermediate of the highly potent antitumor agent ansamitocin, is described, which twice utilizes the Nagao acetate aldol reaction, as well as an indium-mediated alkynylation of a benzyl bromide followed by carboalumination. The key step is a Heck reaction between two terminal alkenes for merging the two major fragments.

  DOI：

  10.1021/ol052588q