methyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1→2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1→2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside | 189745-77-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1→2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1→2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside
• 英文别名: methyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1→2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl(1→2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside；methyl 2-O-(2-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside；Bn(-3)[Bn(-4)][Bn(-6)]Man2Ac(a1-2)[Bn(-3)][Bn(-4)][Bn(-6)]Man(a1-2)[Bn(-3)][Bn(-4)][Bn(-6)]a-Man1Me；[(2R,3S,4S,5R,6R)-2-[(2R,3S,4S,5R,6R)-2-[(2S,3S,4S,5R,6R)-2-methoxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 189745-77-5
• 化学式: C₈₄H₉₀O₁₇
• 分子量: 1371.63
• InChiKey: CNDBHXOPMSFWIM-VIBHCZOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12
• 重原子数：
  101
• 可旋转键数：
  37
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  165
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  methyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1→2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1→2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside 在 甲醇 、 sodium methylate 、 Amberlite IR-120 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 1.0h， 以50%的产率得到methyl 3,4,6-tri-O-benzyl-2-O-(2-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Sonication-Assisted Oligomannoside Synthesis

  摘要：

  We have investigated the use of sonication for the synthesis of oligomannosides. A convenient sonication-mediated glycosylation protocol that is applicable to traditional glycosylation methods has been developed. This protocol can be applicable for activating glycosyl donors that are known to have low reactivity which enable the synthesis of oligomannosides of particular biological interest with the same efficiency.

  DOI：

  10.1021/jo8019835
• 作为产物：
  描述：

  methyl O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1<*>2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside 、 phenyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到methyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1→2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1→2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Sonication-Assisted Oligomannoside Synthesis

  摘要：

  We have investigated the use of sonication for the synthesis of oligomannosides. A convenient sonication-mediated glycosylation protocol that is applicable to traditional glycosylation methods has been developed. This protocol can be applicable for activating glycosyl donors that are known to have low reactivity which enable the synthesis of oligomannosides of particular biological interest with the same efficiency.

  DOI：

  10.1021/jo8019835

文献信息

• Basu, Nabamita; Mukherjee, Mana Mohan; Chaudhury, Aritra, Journal of the Indian Chemical Society, 2013, vol. 90, # 10, p. 1815 - 1820
  作者：Basu, Nabamita、Mukherjee, Mana Mohan、Chaudhury, Aritra、Ghosh, Rina

  DOI：——

  日期：——
• Repetitive Solid Phase Glycosylation on an Alkyl Thiol Polymer Leading to Sugar Oligomers Containing 1,2-<i>trans</i>- and 1,2-<i>cis</i>-Glycosidic Linkages
  作者：Jörg Rademann、Richard R. Schmidt

  DOI：10.1021/jo970087f

  日期：1997.5.1

  Repetitive solid phase glycosylation with sugar trichloroacetimidates is performed on an alkyl thiol polymer, demonstrating the selective formation of glycosidic bonds. The alpha-mannose and alpha-fucose linkages representing examples of 1,2-trans- and 1,2-cis-glycosides are synthesized. It is shown that the presented system can be operated in a cyclic manner, thus allowing many consecutive reaction steps to be performed on the solid support. Reaction conditions for solid phase glycosylation and deprotection are described. Analysis of all solid phase reactions is performed by MALDI-TOF mass spectrometry; the yield of solid phase glycosylation is quantitative up to the tetrameric stage judged from the mass spectra obtained from partial product cleavage after each reaction. Cleavage conditions for analysis and preparative isolation by thiophilic Lewis acids and oxidative methods are optimized.