methyl 4,6-O-benzylidene-2-S-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-2-thio-α-D-mannopyranoside | 215653-60-4

• 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: methyl 4,6-O-benzylidene-2-S-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-2-thio-α-D-mannopyranoside
• CAS: 215653-60-4
• 化学式: C₂₈H₃₆O₁₄S
• 分子量: 628.651
• InChiKey: DJMTYSQUAIUWCE-MWENOWERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.02
• 重原子数：
  43.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  171.58
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  methyl 4,6-O-benzylidene-2-S-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-2-thio-α-D-mannopyranoside 在 溶剂黄146 作用下， 反应 4.5h， 生成 Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2S,3S,4S,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-ylsulfanyl)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Synthesis of heteroanalogues of disaccharides as potential inhibitors of the processing mannosidase Class I enzymes

  摘要：

  Three disaccharide analogues of alpha-D -Man-(l-->2)-alpha-D-Man-OMe in which the ring and/or glycosidic oxygen atoms have been replaced by sulfur have been synthesized as potential inhibitors of Class I mannosidase enzymes. Glycosylation of appropriately protected methyl alpha-D-mannopyranosides, having free alcohol or thiol functional groups at the 2-position, with 2,3,4,6-tetra-O-acetyl-5-thio-alpha-D-mannopyranosyl trichloroacetitmidate was selective for the synthesis of cr-linked disaccharides in the case of the 2-alcohols, but yielded an alpha/beta mixture in the case of the 2-thiol glycosyl accepters. A disaccharide containing a single sulfur in the linkage was synthesized by nucleophilic substitution of the 2-triflate of a methyl alpha-D-glucopyranoside derivative by the thiolate anion of 2,3,4,6-tetra-O-acetyl-1-thio-alpha-D-mannopyranose. Protecting groups were removed by standard methods to give the free heterosubstituted disaccharides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00162-1
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 、 methyl 4,6-O-benzylidene-2-O-trifluoromethanesulfonyl-α-D-glucopyranoside 在 4 A molecular sieve 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以46%的产率得到methyl 4,6-O-benzylidene-2-S-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-2-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of heteroanalogues of disaccharides as potential inhibitors of the processing mannosidase Class I enzymes

  摘要：

  Three disaccharide analogues of alpha-D -Man-(l-->2)-alpha-D-Man-OMe in which the ring and/or glycosidic oxygen atoms have been replaced by sulfur have been synthesized as potential inhibitors of Class I mannosidase enzymes. Glycosylation of appropriately protected methyl alpha-D-mannopyranosides, having free alcohol or thiol functional groups at the 2-position, with 2,3,4,6-tetra-O-acetyl-5-thio-alpha-D-mannopyranosyl trichloroacetitmidate was selective for the synthesis of cr-linked disaccharides in the case of the 2-alcohols, but yielded an alpha/beta mixture in the case of the 2-thiol glycosyl accepters. A disaccharide containing a single sulfur in the linkage was synthesized by nucleophilic substitution of the 2-triflate of a methyl alpha-D-glucopyranoside derivative by the thiolate anion of 2,3,4,6-tetra-O-acetyl-1-thio-alpha-D-mannopyranose. Protecting groups were removed by standard methods to give the free heterosubstituted disaccharides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00162-1