benzyl α-D-mannopyranosyl-(1->3)-α-D-mannopyranosyl-(1->6)-[α-D-mannopyranosyl-(1->6)-α-D-mannopyranosyl-(1->3)]-α-D-mannopyranoside | 1312425-31-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl α-D-mannopyranosyl-(1->3)-α-D-mannopyranosyl-(1->6)-[α-D-mannopyranosyl-(1->6)-α-D-mannopyranosyl-(1->3)]-α-D-mannopyranoside
• 英文别名: Man(a1-6)Man(a1-3)[Man(a1-3)Man(a1-6)]Man(a)-O-Bn；(2S,3S,4S,5S,6R)-2-[[(2R,3S,4S,5S,6R)-6-[(2R,3R,4S,5S,6S)-2-[[(2S,3S,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,5-dihydroxy-6-phenylmethoxyoxan-4-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1312425-31-2
• 化学式: C₃₇H₅₈O₂₆
• 分子量: 918.852
• InChiKey: QLWQPSDTPAVGEQ-XJTMGFQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8
• 重原子数：
  63
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  416
• 氢给体数：
  16
• 氢受体数：
  26

反应信息

• 作为产物：
  描述：

  benzyl 6-O-(2,4,6-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranosyl)-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-α-D-mannopyranoside 在 氨 作用下， 以 甲醇 为溶剂， 反应 144.0h， 以80%的产率得到benzyl α-D-mannopyranosyl-(1->3)-α-D-mannopyranosyl-(1->6)-[α-D-mannopyranosyl-(1->6)-α-D-mannopyranosyl-(1->3)]-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