benzyl 3-O-methyl-2-O-(thiomethoxythiocarbonyl)-α-L-rhamnopyranoside | 144296-83-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 3-O-methyl-2-O-(thiomethoxythiocarbonyl)-α-L-rhamnopyranoside
• 英文别名: O-[(2R,3R,4R,5S,6S)-5-hydroxy-4-methoxy-6-methyl-2-phenylmethoxyoxan-3-yl] methylsulfanylmethanethioate
• CAS: 144296-83-3
• 化学式: C₁₆H₂₂O₅S₂
• 分子量: 358.48
• InChiKey: RQEAPHJFUKYNQQ-VNUKXSOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl 3-O-methyl-2-O-(thiomethoxythiocarbonyl)-α-L-rhamnopyranoside 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 以82%的产率得到benzyl 2-deoxy-3-O-methyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Alternative Syntheses of L-(-)-Oleandrose from L-Rhamnose¹Preparation of Glycals

  摘要：

  L-Rhamnal (2) is prepared from L-rhamnose (3) by use of an improved generalized Fischer-Zach reaction. L-Rhamnal (2) is then converted to L-(-)-oleandrose (1) by stannylene mediated selective methylation and effective hydration. Benzyl alpha-L-oleandrose (12) is prepared by selective methylation and deoxygenation of L-rhamnose (3).

  DOI：

  10.1080/00397919208021642
• 作为产物：
  描述：

  benzyl α-L-rhamnopyranoside 在 dibutylstannoxane 、 sodium hydride 作用下， 反应 3.0h， 生成 benzyl 3-O-methyl-2-O-(thiomethoxythiocarbonyl)-α-L-rhamnopyranoside
  参考文献：
  名称：

  Alternative Syntheses of L-(-)-Oleandrose from L-Rhamnose¹Preparation of Glycals

  摘要：

  L-Rhamnal (2) is prepared from L-rhamnose (3) by use of an improved generalized Fischer-Zach reaction. L-Rhamnal (2) is then converted to L-(-)-oleandrose (1) by stannylene mediated selective methylation and effective hydration. Benzyl alpha-L-oleandrose (12) is prepared by selective methylation and deoxygenation of L-rhamnose (3).

  DOI：

  10.1080/00397919208021642

文献信息

• Alternative Syntheses of L-(-)-Oleandrose from L-Rhamnose¹Preparation of Glycals
  作者：Martin W. Bredenkamp、Cedric W. Holzapfel、Francois Toerien

  DOI：10.1080/00397919208021642

  日期：1992.9

  L-Rhamnal (2) is prepared from L-rhamnose (3) by use of an improved generalized Fischer-Zach reaction. L-Rhamnal (2) is then converted to L-(-)-oleandrose (1) by stannylene mediated selective methylation and effective hydration. Benzyl alpha-L-oleandrose (12) is prepared by selective methylation and deoxygenation of L-rhamnose (3).