methyl O-[4,6-O-(di-tert-butyl)silanediyl-2,3-dideoxy-α-D-threo-hex-2-enopyranosyl]-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl O-[4,6-O-(di-tert-butyl)silanediyl-2,3-dideoxy-α-D-threo-hex-2-enopyranosyl]-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
• 英文别名: (4aR,6S,8aR)-2,2-ditert-butyl-6-[[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3,2]dioxasiline
• 化学式: C₄₂H₅₆O₉Si
• 分子量: 732.987
• InChiKey: KJGLWFNRKHHIHH-UPCZDQDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.87
• 重原子数：
  52
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  83.1
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (2R,3R,4R)-2-(羟基甲基)-3,4-二氢-2H-吡喃-3,4-二醇 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 methyl O-[4,6-O-(di-tert-butyl)silanediyl-2,3-dideoxy-α-D-threo-hex-2-enopyranosyl]-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Trichloroacetimidate as a Leaving Group in the Ferrier Rearrangement: Highly Stereoselective Synthesis of Pseudogalactal Glycosides

  摘要：

  The Ferrier rearrangement of a galactal derivative 2 bearing the trichloroacetimidate functionality as a leaving group at the C-3 position was performed in the presence of trimethylsilyl triflate as catalyst; the corresponding pseudogalactal glycosides were obtained in excellent yield and stereoselectivity with a wide range of acceptors.

  DOI：

  10.1002/1099-0690(200202)2002:4<713::aid-ejoc713>3.0.co;2-q

文献信息

• Trichloroacetimidate as a Leaving Group in the Ferrier Rearrangement: Highly Stereoselective Synthesis of Pseudogalactal Glycosides
  作者：Adel A.-H. Abdel-Rahman、Gottfried A. Winterfeld、Mohamed Takhi、Richard R. Schmidt

  DOI：10.1002/1099-0690(200202)2002:4<713::aid-ejoc713>3.0.co;2-q

  日期：2002.2

  The Ferrier rearrangement of a galactal derivative 2 bearing the trichloroacetimidate functionality as a leaving group at the C-3 position was performed in the presence of trimethylsilyl triflate as catalyst; the corresponding pseudogalactal glycosides were obtained in excellent yield and stereoselectivity with a wide range of acceptors.