prop-2-enyl N-[(3S,4S,6S)-6-[(2S,3R,4R,5S,6R)-5-[6-[tert-butyl(dimethyl)silyl]oxy-9H-pyrido[3,4-b]indole-1-carbonyl]-2-methoxy-6-methyl-5-methylsulfanyl-4-(naphthalen-2-ylmethoxy)oxan-3-yl]oxy-4-methoxyoxan-3-yl]-N-propan-2-ylcarbamate | 1313188-78-1

• 分子结构分类: 有机化合物
• 英文名称: prop-2-enyl N-[(3S,4S,6S)-6-[(2S,3R,4R,5S,6R)-5-[6-[tert-butyl(dimethyl)silyl]oxy-9H-pyrido[3,4-b]indole-1-carbonyl]-2-methoxy-6-methyl-5-methylsulfanyl-4-(naphthalen-2-ylmethoxy)oxan-3-yl]oxy-4-methoxyoxan-3-yl]-N-propan-2-ylcarbamate
• CAS: 1313188-78-1
• 化学式: C₅₀H₆₅N₃O₁₀SSi
• 分子量: 928.232
• InChiKey: OVOPGKHSBKWKBU-JXHVFMIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.06
• 重原子数：
  65
• 可旋转键数：
  18
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  165
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  prop-2-enyl N-[(3S,4S,6S)-6-[(2S,3R,4R,5S,6R)-5-[[6-[tert-butyl(dimethyl)silyl]oxy-9H-pyrido[3,4-b]indol-1-yl]-hydroxymethyl]-2-methoxy-6-methyl-5-methylsulfanyl-4-(naphthalen-2-ylmethoxy)oxan-3-yl]oxy-4-methoxyoxan-3-yl]-N-propan-2-ylcarbamate 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以74%的产率得到prop-2-enyl N-[(3S,4S,6S)-6-[(2S,3R,4R,5S,6R)-5-[6-[tert-butyl(dimethyl)silyl]oxy-9H-pyrido[3,4-b]indole-1-carbonyl]-2-methoxy-6-methyl-5-methylsulfanyl-4-(naphthalen-2-ylmethoxy)oxan-3-yl]oxy-4-methoxyoxan-3-yl]-N-propan-2-ylcarbamate
  参考文献：
  名称：

  Synthesis of the Carboline Disaccharide Domain of Shishijimicin A

  摘要：

  A synthetic route to the carboline disaccharide domain (2) of shishljlmicin A (1) has been developed. The convergent synthesis relies on a novel application of the Reetz-Muller-Starke reaction to form the central, sulfur-bearing quaternary carbon center and addition of the carboline structural motif as a dianion to a disaccharide aldehyde fragment.

  DOI：

  10.1021/ol201444t