allyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->4)-6-O-tert-butyldimethylsilyl-α-D-mannopyranoside | 1055301-36-4

• 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: allyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->4)-6-O-tert-butyldimethylsilyl-α-D-mannopyranoside
• 英文别名: Bz(-2)[Bz(-3)][Bz(-4)][Bz(-6)]Man(a1-4)[TBDPS(-6)]Man(a)-O-allyl；[(2R,3R,4S,5S,6R)-3,4,5-tribenzoyloxy-6-[(2R,3S,4R,5S,6S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-4,5-dihydroxy-6-prop-2-enoxyoxan-3-yl]oxyoxan-2-yl]methyl benzoate
• CAS: 1055301-36-4
• 化学式: C₅₉H₆₀O₁₅Si
• 分子量: 1037.2
• InChiKey: KEMCDZFMHGQKLC-ANTNBPECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.86
• 重原子数：
  75
• 可旋转键数：
  24
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  192
• 氢给体数：
  2
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  allyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->4)-6-O-tert-butyldimethylsilyl-α-D-mannopyranoside 、 乙酸酐 在 吡啶 作用下， 生成 allyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->4)-2,3-di-O-acetyl-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
• 作为产物：
  描述：

  allyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->4)-6-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-α-D-mannopyranoside 在 对甲苯磺酸 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 2.5h， 以42%的产率得到allyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->4)-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

文献信息

• Comparative investigations on the regioselective mannosylation of 2,3,4-triols of mannose
  作者：Piotr Cmoch、Zbigniew Pakulski

  DOI：10.1016/j.tetasy.2008.05.032

  日期：2008.6

  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.