benzyl 3-O-(2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranosyl)-4-O-acetyl-6-O-trimethylsilyl-α-D-mannopyranoside | 1312425-30-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 3-O-(2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranosyl)-4-O-acetyl-6-O-trimethylsilyl-α-D-mannopyranoside
• CAS: 1312425-30-1
• 化学式: C₅₉H₆₈O₂₄Si
• 分子量: 1189.26
• InChiKey: XECZFSLYLRARGN-CPIUGCFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.96
• 重原子数：
  84.0
• 可旋转键数：
  23.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  295.24
• 氢给体数：
  1.0
• 氢受体数：
  24.0

反应信息

• 作为产物：
  描述：

  三氟甲磺酸三甲基硅酯 、 benzyl 3-O-(2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranosyl)-4-O-acetyl-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside 在 三氟甲磺酸 作用下， 生成 、 benzyl 3-O-(2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranosyl)-4-O-acetyl-6-O-trimethylsilyl-α-D-mannopyranoside
  参考文献：
  名称：

  Four-component one-pot synthesis of a branched manno-pentasaccharide: tert-butyldiphenylsilyl ether as an in situ removable carbohydrate-protecting group

  摘要：

  A branched mannose-pentasaccharide was synthesized in a convergent one-pot sequence involving chemo- and regioselective glycosylations of suitable acceptors and in situ removal of tert-butyldiphenylsilyl group. The process demonstrated that a combination of TMSOTf and TfOH can be used as an effective reagent for the fast and selective in situ de-protection of tert-butyldiphenylsilyl group, and also serve as part of the promoter system for the subsequent glycosylation reaction. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.109