methyl 2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-glucopyranoside | 129948-14-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-glucopyranoside
• 英文别名: methyl 3,4,6-tri-O-benzyl-2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside
• CAS: 129948-14-7；131283-77-7
• 化学式: C₄₂H₅₀O₁₅
• 分子量: 794.85
• InChiKey: GLLPEKWSDULFDW-GCPPGDMWSA-N

物化性质

• 沸点：
  790.5±60.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.21
• 重原子数：
  57.0
• 可旋转键数：
  18.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  169.81
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  methyl 2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-glucopyranoside 在 palladium on activated charcoal 氢气 、 sodium methylate 作用下， 以 甲醇 、 乙醇 、 溶剂黄146 为溶剂， 25.0 ℃ 、350.0 kPa 条件下， 反应 2.0h， 生成 а1,2-单甘露醇,а甲基糖苷
  参考文献：
  名称：

  Lysosomal-enzyme targeting: the phosphorylation of synthetic d-mannosyl saccharides by UDP-N-acetylglucosamine:lysosomal-enzyme N-acetylglucosaminephosphotransferase from rat-liver microsomes and fibroblasts

  摘要：

  Phosphorylation of the D-mannose residues of lysosomal enzymes is essential for the uptake and intracellular transport of these enzymes to lysosomes. The GlcNAc-P-transferase which is involved in the phosphorylation reaction seems to recognize a signal, probably a protein conformation, common to many lysosomal enzymes. To evaluate the role of the carbohydrate portion of the enzyme in these phosphorylation reactions, the acceptor specificity of GlcNAc-P-transferase from rat-liver microsomes and fibroblasts was examined with the aid of synthetic D-mannosyl disaccharides and derivatives that are closely related to the high-mannose type of oligosaccharides. Four methyl D-mannobiosides were synthesized, and their structures were established by 13C-n.m.r. spectroscopy. Of all the D-mannosyl saccharides tested, alpha-D-Man-(1----2)-alpha-D-Man-(1----OMe) was found to be the best acceptor, thereby suggesting that oligosaccharide structure may also have a role to play in recognition by this enzyme.

  DOI：

  10.1016/s0008-6215(00)90298-2
• 作为产物：
  描述：

  methyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside 、 S-ethyl 2,3,4,6-tetra-O-acetyl-1-deoxy-1-thio-α-D-mannopyranoside 在 辛酸铑 、 methyl 2-(4-chlorophenyl)-2-diazoacetate 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以84%的产率得到methyl 2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  通过连续的铑 (II) 和布朗斯台德酸催化实现糖基化

  摘要：

  在此，我们报道了一种高效的糖基化反应，包括两个按时间顺序精心设计的催化循环：1）铑催化形成锍叶立德；2) Brønsted 酸催化形成锍离子。该协议强调了一种有效且稳健的策略，可从适合糖基化的糖基锍叶立德前体制备糖基锍离子。

  DOI：

  10.1021/jacs.9b04619