(2'S,3'S)-benzyl 3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-O-tert-butyldimethylsilyl-α-D-mannopyranoside | 1055301-56-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: (2'S,3'S)-benzyl 3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-O-tert-butyldimethylsilyl-α-D-mannopyranoside
• CAS: 1055301-56-8
• 化学式: C₃₅H₄₆O₈Si
• 分子量: 622.831
• InChiKey: TZDAOFZRKGFYHL-MPBLAVPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.37
• 重原子数：
  44.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  84.84
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2'S,3'S)-benzyl 3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-O-tert-butyldimethylsilyl-α-D-mannopyranoside 、 [(2R,3R,4S,5S,6S)-3,4,5-三苯甲酰氧基-6-(2,2,2-三氯亚氨代乙酰)氧基-四氢吡喃-2-基]甲基苯甲酸酯 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以53%的产率得到benzyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->2)-6-O-tert-butyldimethylsilyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Comparative investigations on the regioselective mannosylation of 2,3,4-triols of mannose

  摘要：

  Regioselective glycosylation of 2,3,4-unprotected benzyl alpha-D-mannopyranoside and allyl alpha- and -beta-D-mannopyranosides has been investigated. The configuration at the anomeric centre influences the outcome of the reaction. Possible role of hydrogen-bonding network in glycosylation of the above triols used as glycosidic acceptors is discussed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.05.032
• 作为产物：
  描述：

  (2'S,3'S)-benzyl 3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-α-D-mannopyranoside 、 叔丁基二苯基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以89%的产率得到(2'S,3'S)-benzyl 3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-O-tert-butyldimethylsilyl-α-D-mannopyranoside
  参考文献：
  名称：

  Comparative investigations on the regioselective mannosylation of 2,3,4-triols of mannose

  摘要：

  Regioselective glycosylation of 2,3,4-unprotected benzyl alpha-D-mannopyranoside and allyl alpha- and -beta-D-mannopyranosides has been investigated. The configuration at the anomeric centre influences the outcome of the reaction. Possible role of hydrogen-bonding network in glycosylation of the above triols used as glycosidic acceptors is discussed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.05.032