methyl 2,4-di-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-α-D-mannopyranoside

• 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: methyl 2,4-di-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-α-D-mannopyranoside
• 英文别名: Bz(-2)[Bz(-3)][Bz(-4)][Bz(-6)]Man(a1-6)[Bz(-2)][Bz(-4)]a-Man1Me；[(2R,3R,4S,5S,6S)-3,4,5-tribenzoyloxy-6-[[(2R,3S,4S,5S,6S)-3,5-dibenzoyloxy-4-hydroxy-6-methoxyoxan-2-yl]methoxy]oxan-2-yl]methyl benzoate
• 化学式: C₅₅H₄₈O₁₇
• 分子量: 980.976
• InChiKey: RMPSKFKSSBZZQS-RKYBMZJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  72
• 可旋转键数：
  23
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  215
• 氢给体数：
  1
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  甲基-D-丙噻 在 三氟甲磺酸三甲基硅酯 、 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.67h， 生成 methyl 2,4-di-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-α-D-mannopyranoside
  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

• Methyl 1,2-Orthoesters as Useful Glycosyl Donors in Glycosylation Reactions: A Comparison with n-Pent-4-enyl 1,2-Orthoesters
  作者：Clara Uriel、Juan Ventura、Ana M. Gómez、J. Cristóbal López、Bert Fraser-Reid

  DOI：10.1002/ejoc.201200089

  日期：2012.6

  Mannopyranose-derived methyl 1,2-orthoacetates (R = Me) and -benzoates (R = Ph) can function as glycosyl donors – upon BF3·Et2O activation in CH2Cl2 – in glycosylation reactions with monosaccharide acceptors to afford disaccharides in good yields. In the process, glycosylation is preferred to acid-catalyzed rearrangement leading to methyl mannopyranosides. Methyl 1,2-orthoesters can be also used in regioselective

  吡喃甘露糖衍生的 1,2- 原乙酸甲酯 (R = Me) 和 -苯甲酸酯 (R = Ph) 可以作为糖基供体 - 在 CH2Cl2 中 BF3·Et2O 活化后 - 在与单糖受体的糖基化反应中以良好的收率提供二糖。在该过程中，糖基化优于酸催化重排，导致甲基吡喃甘露糖苷。甲基 1,2-原酸酯也可用于单糖二醇的区域选择性糖基化方案，其中它们显示出良好的区域选择性。
• Relevance of the Glycosyl Donor to the Regioselectivity of Glycosidation of Primary-Secondary Diol Acceptors and Application of These Ideas to in Situ Three-Component Double Differential Glycosidation
  作者：Clara Uriel、Attila Agocs、Ana M. Gómez、J. Cristóbal López、Bert Fraser-Reid

  DOI：10.1021/ol0518232

  日期：2005.10.1

  have been exposed to armed, disarmed, and n-pentenyl ortho ester glycosyl donors in glycosidation reactions. It is shown that the regioselectivity of those glycosylations is greatly influenced by the armed, disarmed, or ortho ester nature of the glycosyl donors. The selectivities observed have been used to devise efficient in situ three-component glycosylations involving two donors and one acceptor.

  [反应：见正文]在糖基化反应中，三对伯-仲二醇受体已暴露于武装，解除武装和正戊烯基原酸酯糖基供体。结果表明，那些糖基化的区域选择性受到糖基供体的武装，解除武装或原酸酯性质的极大影响。观察到的选择性已用于设计有效的原位三组分糖基化反应，涉及两个供体和一个受体。
• 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.