methyl 3-O-<2-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl>-6-O-<3,6-di-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-2,4-di-O-benzyl-α-D-mannopyranosyl>-2,4-di-O-benzyl-α-D-mannopyranoside | 80738-59-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-<2-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl>-6-O-<3,6-di-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-2,4-di-O-benzyl-α-D-mannopyranosyl>-2,4-di-O-benzyl-α-D-mannopyranoside
• 英文别名: methyl 3-O-(2-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-6-O-(3,6-di-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-2,4-di-O-benzyl-α-D-mannopyranosyl)-2,4-di-O-benzyl-α-D-mannopyranoside；methyl 3-O-[2-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl]-6-O-[3,6-di-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-2,4-di-O-benzyl-α-D-mannopyranosyl]-2,4-di-O-benzyl-α-D-mannopyranoside；Bn(-3)[Bn(-4)][Bn(-6)]Man2Ac(a1-2)[Bn(-3)][Bn(-4)][Bn(-6)]Man(a1-3)[Bn(-3)[Bn(-4)][Bn(-6)]Man2Ac(a1-3)[Bn(-3)[Bn(-4)][Bn(-6)]Man2Ac(a1-6)][Bn(-2)][Bn(-4)]Man(a1-6)][Bn(-2)][Bn(-4)]a-Man1Me；[(2S,3S,4S,5R,6R)-2-[[(2R,3R,4S,5S,6S)-4-[(2R,3S,4S,5R,6R)-3-acetyloxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-6-[[(2R,3R,4S,5S,6S)-4-[(2R,3S,4S,5R,6R)-3-[(2R,3S,4S,5R,6R)-3-acetyloxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-6-methoxy-3,5-bis(phenylmethoxy)oxan-2-yl]methoxy]-3,5-bis(phenylmethoxy)oxan-2-yl]methoxy]-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 80738-59-6
• 化学式: C₁₅₅H₁₆₆O₃₄
• 分子量: 2573.0
• InChiKey: UHDDGMAAVHLKQW-YFKSVDIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20.9
• 重原子数：
  189
• 可旋转键数：
  71
• 环数：
  22.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  337
• 氢给体数：
  0
• 氢受体数：
  34

反应信息

• 作为反应物：
  描述：

  methyl 3-O-<2-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl>-6-O-<3,6-di-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-2,4-di-O-benzyl-α-D-mannopyranosyl>-2,4-di-O-benzyl-α-D-mannopyranoside 在 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 7.0h， 以96.3%的产率得到methyl 2,4-di-O-benzyl-3-O-<3,4,6-tri-O-benzyl-2-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranosyl>-6-O-<2,4-di-O-benzyl-3,6-di-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranosyl>-α-D-mannopyranoside
  参考文献：
  名称：

  糖蛋白聚糖链的重建：甘露糖苷和甘露糖苷的分支

  摘要：

  描述了使用适当保护的甘露糖苷13作为关键中间体来合成分支甘露糖苷4和甘露六糖苷5的途径。

  DOI：

  10.1016/s0040-4020(01)92346-4
• 作为产物：
  描述：

  methyl 2,4-di-O-benzyl-6-O-(2,4-di-O-benzyl-α-D-mannopyranosyl)-3-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-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53%的产率得到methyl 3-O-<2-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl>-6-O-<3,6-di-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-2,4-di-O-benzyl-α-D-mannopyranosyl>-2,4-di-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