methyl 2,3,4-tri-O-benzyloxycarbonyl-α-D-mannopyranoside | 191332-84-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzyloxycarbonyl-α-D-mannopyranoside
• 英文别名: benzyl [(2R,3R,4S,5S,6S)-2-(hydroxymethyl)-6-methoxy-3,5-bis(phenylmethoxycarbonyloxy)oxan-4-yl] carbonate
• CAS: 191332-84-0
• 化学式: C₃₁H₃₂O₁₂
• 分子量: 596.588
• InChiKey: ZDDPVGVMEWNWEE-MASCHLQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  43
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  145
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzyloxycarbonyl-α-D-mannopyranoside 在 palladium on activated charcoal 吡啶 、 氢气 、 silica gel 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 52.0h， 生成 methyl 4-O-benzoyl-α-D-mannopyranoside
  参考文献：
  名称：

  The benzyloxycarbonyl group: An alternative protective group in the mannose series

  摘要：

  A procedure for the O-benzyloxycarbonylation at positions 2-4 in the mannose series is described. Starting from methyl 6-O-(4-methoxy)trityl-alpha-D-mannopyranoside methyl 2,3,4-tri-O-benzyloxycarbonyl-6-O-(4-methoxy)tyrityl-alpha-D-mannopyranoside was obtained. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00329-1
• 作为产物：
  描述：

  甲基-D-丙噻 在 吡啶 、 4-二甲氨基吡啶 、 ammonium cerium(IV) nitrate 、 水 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 76.0h， 生成 methyl 2,3,4-tri-O-benzyloxycarbonyl-α-D-mannopyranoside
  参考文献：
  名称：

  The benzyloxycarbonyl group: An alternative protective group in the mannose series

  摘要：

  A procedure for the O-benzyloxycarbonylation at positions 2-4 in the mannose series is described. Starting from methyl 6-O-(4-methoxy)trityl-alpha-D-mannopyranoside methyl 2,3,4-tri-O-benzyloxycarbonyl-6-O-(4-methoxy)tyrityl-alpha-D-mannopyranoside was obtained. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00329-1

文献信息

• Selective Removal of Benzyl Carbonate Used as a Protecting Group in Carbohydrate Chemistry
  作者：Fouzi Mouffouk、Alain Morère、Sébastien Vidal、Alain Leydet、Jean-Louis Montero

  DOI：10.1081/scc-120027267

  日期：2004.1

  Abstract It has been demonstrated that benzyl carbonate protecting group is orthogonal with tert-butyldimethylsilyl and (4-methoxy)trityl ethers. Moreover, benzyl carbonates can be selectively cleaved using aminolysis conditions.

  摘要 已经证明碳酸苄酯保护基团与叔丁基二甲基甲硅烷基和(4-甲氧基)三苯甲基醚正交。此外，可以使用氨解条件选择性地裂解碳酸苄酯。
• The Benzyloxycarbonyl Protective Group : a Good Alternative to the Benzyl Protective Group in the Glycopyranoside and Glycofuranoside Series
  作者：Alain Morère、Fouzi Mouffouk、Claude Chavis、Jean-Louis Montero

  DOI：10.1016/s0040-4039(97)10021-1

  日期：1997.10

  A procedure for the O-benzyloxycarbonylation of secondary alcohols in the glucose, galactose, mannose, ribose and deoxyribose series is described. Starting from the (4-methoxy)tritylated derivatives on the primary hydroxyl group, the fully protected compounds were obtained for the first time in high yields. (C) 1997 Published by Elsevier Science Ltd.
• The benzyloxycarbonyl group: An alternative protective group in the mannose series
  作者：Alain Morère、Chantal Menut、Carole Vidil、Philip Skaanderup、Jesper Thorsen、Jean-Pierre Roque、Jean-Louis Montero

  DOI：10.1016/s0008-6215(96)00329-1

  日期：1997.5

  A procedure for the O-benzyloxycarbonylation at positions 2-4 in the mannose series is described. Starting from methyl 6-O-(4-methoxy)trityl-alpha-D-mannopyranoside methyl 2,3,4-tri-O-benzyloxycarbonyl-6-O-(4-methoxy)tyrityl-alpha-D-mannopyranoside was obtained. (C) 1997 Elsevier Science Ltd.