1,2,3-Tri-O-acetyl-4,6-di-O-benzyl-β-D-mannopyranose | 88261-72-7

• 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: 1,2,3-Tri-O-acetyl-4,6-di-O-benzyl-β-D-mannopyranose
• 英文别名: 1,2,3-tri-O-acetyl-4,6-di-O-benzyl-D-mannopyranose
• CAS: 88261-72-7
• 化学式: C₂₆H₃₀O₉
• 分子量: 486.519
• InChiKey: SJXQMCOFHFNDTM-PUHDZGQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  35.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  106.59
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  methyl 4,6-di-O-benzyl-α-D-mannopyranoside 在 吡啶 、 三氟乙酸 作用下， 反应 4.5h， 生成 1,2,3-Tri-O-acetyl-4,6-di-O-benzyl-β-D-mannopyranose
  参考文献：
  名称：

  Synthesis of a Pentasaccharide Epitope for the Investigation of Carbohydrate-Protein Interactions

  摘要：

  Pyranose residues of a polysaccharide that are not involved in the principal sugar-protein antibody combining site, filled by trisaccharide 1, cause a 50-fold reduction in intrinsic affinity. The antibody is crystallographically characterized, and the residue responsible for the lost binding energy has been identified as the terminal disaccharide Rha-->Gal of pentasaccharide 5. This disaccharide segment of 5 may avoid protein contact by adopting the ''anti'' conformer about the preceding Man-Rha glycosidic linkage. Monosaccharide thioglycoside synthons 6-9 were used in NIS-promoted glycosylations to synthesize the pentasaccharide as a glycoside that was suitable for binding and solution conformational studies. Disaccharide 29 was obtained upon the addition of rhamnose building unit 6 to the (trimethylsilyl)ethyl galactopyranoside 10 followed by protecting group manipulation. The sequential addition of 7-9 to 29 afforded the pentasaccharide derivative 35 bearing a 2-O-benzoate group suited for subsequent 1,2-trans-glycoside synthesis following its conversion to a glycosyl imidate. In order to preserve the integrity of the 3,6-dideoxyhexopyranosyl glycosidic bond during cleavage of the (trimethylsilyl)ethyl group leading to the imidate 39, it was essential to convert the benzylated pentasaccharide target 35 into its fully acylated derivative 37. Pentasaccharide 5 was obtained by transesterification of the protected glycoside 40 formed via 39. Qualitative NOE measurements suggest a predominant solution conformation for 5 that cannot be adopted in the bound state due to protein-oligosaccharide clashes at the periphery of the binding site.

  DOI：

  10.1021/jo00127a043

文献信息

• A synthesis of 3-O-(α-d-mannopyranosyl)-d-mannose and its protein conjugate
  作者：Laila Fathy Awad、El Sayed H. El Ashry、Conrad Schuerch

  DOI：10.1016/0008-6215(83)88407-9

  日期：1983.10

  number of sequences. Glycosidations with 2,3-di-O-acetyl-4,6-di-O-benzyl-d-mannopyranosyl and 2-O-benzoyl-3,4,6-tri-O-benzyl-d-mannopyranosyl p-toluenesulfonates were found to give better yields than the Helferich modification, the use of a peracylated d-mannopyranosyl halide, or the use of triflyl leaving group. Only the α anomer was obtained. Factors influencing glycosidation reactions are discussed

  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。