(2R,3R,4R,5R,6S)-6-methoxy-2-methyl-3-methylsulfanyl-4-(naphthalen-2-ylmethoxy)-5-prop-2-enoxyoxane-3-carbonitrile | 1313188-89-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2R,3R,4R,5R,6S)-6-methoxy-2-methyl-3-methylsulfanyl-4-(naphthalen-2-ylmethoxy)-5-prop-2-enoxyoxane-3-carbonitrile
• CAS: 1313188-89-4
• 化学式: C₂₃H₂₇NO₄S
• 分子量: 413.538
• InChiKey: HUXFBJSMMJDQLG-CLHYHVNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  86
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (2R,4R,5R,6S)-5-(allyloxy)-6-methoxy-2-methyl-4-(naphthalen-2-ylmethoxy)dihydro-2H-pyran-3(4H)-one 在 三氟甲磺酸三甲基硅酯 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 (2R,3R,4R,5R,6S)-6-methoxy-2-methyl-3-methylsulfanyl-4-(naphthalen-2-ylmethoxy)-5-prop-2-enoxyoxane-3-carbonitrile 、 (2R,3S,4R,5R,6S)-6-methoxy-2-methyl-3-methylsulfanyl-4-(naphthalen-2-ylmethoxy)-5-prop-2-enoxyoxane-3-carbonitrile
  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

文献信息

• Synthesis of the Carboline Disaccharide Domain of Shishijimicin A
  作者：K. C. Nicolaou、J. L. Kiappes、Weiwei Tian、Vijaya B. Gondi、Jochen Becker

  DOI：10.1021/ol201444t

  日期：2011.8.5

  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.