Bz(-2)[Bz(-4)]Man(a1-6)[Bz(-2)][Bz(-4)]Man(a)-N3 | 647830-34-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Bz(-2)[Bz(-4)]Man(a1-6)[Bz(-2)][Bz(-4)]Man(a)-N3
• 英文别名: [(2R,3S,4S,5S,6S)-6-[[(2R,3S,4S,5S,6S)-6-azido-3,5-dibenzoyloxy-4-hydroxyoxan-2-yl]methoxy]-5-benzoyloxy-4-hydroxy-2-(hydroxymethyl)oxan-3-yl] benzoate
• CAS: 647830-34-0
• 化学式: C₄₀H₃₇N₃O₁₄
• 分子量: 783.745
• InChiKey: LSULRIKVVOWXOV-LZGCLKHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  57
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  208
• 氢给体数：
  3
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  2-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl 2,2,2-trichloroacetimidate 、 Bz(-2)[Bz(-4)]Man(a1-6)[Bz(-2)][Bz(-4)]Man(a)-N3 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以70%的产率得到
  参考文献：
  名称：

  Regioselective glycosylation of 3,6-unprotected mannoside derivatives: fast access to high-mannose type oligosaccharides

  摘要：

  A regioselective glycosylation of 3,6-unprotected mannoside acceptors was investigated. With glycosyl trichloroacetimidate donors, when an excess of trimethylsilyl trifluoromethanesulfonate is used as the catalyst, 6-O-glycosylation exclusively occurred affording a silylated disaccharide that could be involved in a subsequent glycosylation reaction. As an illustration, the fast synthesis of two trisaccharides and one pentasaccharide was achieved. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.219
• 作为产物：
  描述：

  2,4-di-O-benzoyl-α-D-mannopyranosyl azide 在 甲醇 、 乙酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 24.5h， 生成 Bz(-2)[Bz(-4)]Man(a1-6)[Bz(-2)][Bz(-4)]Man(a)-N3
  参考文献：
  名称：

  Regioselective glycosylation of 3,6-unprotected mannoside derivatives: fast access to high-mannose type oligosaccharides

  摘要：

  A regioselective glycosylation of 3,6-unprotected mannoside acceptors was investigated. With glycosyl trichloroacetimidate donors, when an excess of trimethylsilyl trifluoromethanesulfonate is used as the catalyst, 6-O-glycosylation exclusively occurred affording a silylated disaccharide that could be involved in a subsequent glycosylation reaction. As an illustration, the fast synthesis of two trisaccharides and one pentasaccharide was achieved. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.219

文献信息

• Regioselective glycosylation of 3,6-unprotected mannoside derivatives: fast access to high-mannose type oligosaccharides
  作者：Nicolas Smiljanic、Sami Halila、Vincent Moreau、Florence Djedaı̈ni-Pilard

  DOI：10.1016/j.tetlet.2003.09.219

  日期：2003.12.8

  A regioselective glycosylation of 3,6-unprotected mannoside acceptors was investigated. With glycosyl trichloroacetimidate donors, when an excess of trimethylsilyl trifluoromethanesulfonate is used as the catalyst, 6-O-glycosylation exclusively occurred affording a silylated disaccharide that could be involved in a subsequent glycosylation reaction. As an illustration, the fast synthesis of two trisaccharides and one pentasaccharide was achieved. (C) 2003 Elsevier Ltd. All rights reserved.