methyl 2,4,6-tri-O-benzyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside | 88261-81-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,4,6-tri-O-benzyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside
• CAS: 88261-81-8
• 化学式: C₄₂H₅₀O₁₅
• 分子量: 794.85
• InChiKey: COWBQDWAFIMTPQ-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 2,4,6-tri-O-benzyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside 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 甲基 3-O-alpha-D-甘露糖基-alpha-D-吡喃甘露糖苷
  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 2,4,6-tri-O-benzyl-α-D-mannopyranoside 、 2,3,4,6-四-O-乙酰基-1-溴-Alpha-D-甘露糖 在 silver trifluoromethanesulfonate 、 1,1,3,3-四甲基脲 作用下， 反应 6.0h， 以36%的产率得到methyl 2,4,6-tri-O-benzyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside
  参考文献：
  名称：

  3-O-（α-d-甘露吡喃糖基）-d-甘露糖的合成及其蛋白结合物

  摘要：

  研究了3-O-（α-d-甘露吡喃糖基）-d-甘露糖和2-（4-氨基苯基）乙基3-O-（α-d-甘露吡喃糖基）-α-d-甘露吡喃糖苷的合成方法。许多序列。2,3-二-O-乙酰基-4,6-二-O-苄基-d-甘露吡喃糖基和2-O-苯甲酰基-3,4,6-三-O-苄基-d-甘露吡喃糖基对甲苯磺酸的糖基化与使用Helferich修饰，使用过酰基化的d-甘露吡喃糖基卤化物或使用triflyl离去基团相比，发现它们的收率更高。仅获得α端基异构体。讨论了影响糖苷化反应的因素。汞（II）配合物用于4,6-二-O-苄基-α-d-甘露吡喃糖苷的选择性2-O-酰化。通过异硫氰酸酯方法制备二糖-蛋白质缀合物。

  DOI：

  10.1016/0008-6215(83)88407-9