1-adamantanyl 2',3'-di-O-benzyl-β-D-mannopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-adamantanyl 2',3'-di-O-benzyl-β-D-mannopyranoside
• 英文别名: (2R,3R,4S,5S,6S)-6-(1-adamantyloxy)-2-(hydroxymethyl)-4,5-bis(phenylmethoxy)oxan-3-ol
• 化学式: C₃₀H₃₈O₆
• 分子量: 494.628
• InChiKey: UEIXWJCKNUKHDV-AWCDIZKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-金刚烷醇 在 三氟甲磺酸酐 、 silica gel 、 sulfobromophthalein sodium 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 生成 1-adamantanyl 2',3'-di-O-benzyl-β-D-mannopyranoside
  参考文献：
  名称：

  Solid-Phase Synthesis of β-Mannosides

  摘要：

  The linkage of S-phenyl 2,3-di-O-benzyl-alpha-D-thiomannopyranoside to a cross-linked polystyrene support in the form of its 4,6-O-polystyrylborinate ester is described. The activation of this polymer-supported mannosyl donor is achieved at -60 degreesC in dichloromethane in the presence of 2,4,6-tri-tert-butylpyrimidine with the combination 1-benzenesulfinyl piperidine and trifluoromethanesulfonic anhydride. Addition of the donor alcohol at -60 degreesC followed by warming to room temperature and subsequent cleavage from the resin by gentle heating in aqueous acetone yields anomerically pure 2,3-di-O-abenZyl-beta-D-mannopyranosides in excellent yield, Successful, diastereoselective coupling is demonstrated with a range of primary, secondary, and tertiary glycosyl acceptors, including typical carbohydrates and threonine derivatives.

  DOI：

  10.1021/ja011406u

文献信息

• Method of forming glycosidic bonds from thioglycosides using an N,N-dialkylsulfinamide
  申请人：——

  公开号：US20040019198A1

  公开（公告）日：2004-01-29

  A method of forming a glycosidic bond utilizing an activated thioglycoside is disclosed. The thioglycoside is activated by an N,N-dialkylsulfinamide and trifluoromethanesulfonic anhydride. The method allows the facile synthesis of disaccharides, oligosacchraides, and polysaccharides in solution or on a polymer support.

  揭示了一种利用活化硫代糖苷键的方法。该硫代糖苷经N,N-二烷基亚磺酰胺和三氟甲磺酸酐激活。该方法允许在溶液中或在聚合物支撑上轻松合成二糖、寡糖和多糖。
• Solid-Phase Synthesis of β-Mannosides
  作者：David Crich、Mark Smith

  DOI：10.1021/ja011406u

  日期：2002.7.1

  The linkage of S-phenyl 2,3-di-O-benzyl-alpha-D-thiomannopyranoside to a cross-linked polystyrene support in the form of its 4,6-O-polystyrylborinate ester is described. The activation of this polymer-supported mannosyl donor is achieved at -60 degreesC in dichloromethane in the presence of 2,4,6-tri-tert-butylpyrimidine with the combination 1-benzenesulfinyl piperidine and trifluoromethanesulfonic anhydride. Addition of the donor alcohol at -60 degreesC followed by warming to room temperature and subsequent cleavage from the resin by gentle heating in aqueous acetone yields anomerically pure 2,3-di-O-abenZyl-beta-D-mannopyranosides in excellent yield, Successful, diastereoselective coupling is demonstrated with a range of primary, secondary, and tertiary glycosyl acceptors, including typical carbohydrates and threonine derivatives.