(2R,3S,4R,5R,6S)-5-hydroxy-6-methoxy-2-methyl-3-methylsulfanyl-4-(naphthalen-2-ylmethoxy)oxane-3-carbonitrile | 1313188-80-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2R,3S,4R,5R,6S)-5-hydroxy-6-methoxy-2-methyl-3-methylsulfanyl-4-(naphthalen-2-ylmethoxy)oxane-3-carbonitrile
• CAS: 1313188-80-5
• 化学式: C₂₀H₂₃NO₄S
• 分子量: 373.473
• InChiKey: UKWUKZLZSSITQJ-CLZYOGPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  97
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5R,6S)-5-hydroxy-6-methoxy-2-methyl-3-methylsulfanyl-4-(naphthalen-2-ylmethoxy)oxane-3-carbonitrile 在 silver perchlorate 、 二异丁基氢化铝 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 prop-2-enyl N-[(3S,4S,6S)-6-[(2S,3R,4R,5S,6R)-5-formyl-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
• 作为产物：
  描述：

  (2R,4R,5R,6S)-6-methoxy-2-methyl-3,3-bis(methylsulfanyl)-4-(naphthalen-2-ylmethoxy)-5-prop-2-enoxyoxane 在 四(三苯基膦)钯 、 四氯化锡 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 5.0h， 生成 (2R,3S,4R,5R,6S)-5-hydroxy-6-methoxy-2-methyl-3-methylsulfanyl-4-(naphthalen-2-ylmethoxy)oxane-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.