methyl 3-O-acetyl-4,6-O-benzylidene-2-thio-α-D-mannopyranoside | 215653-45-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 3-O-acetyl-4,6-O-benzylidene-2-thio-α-D-mannopyranoside
• CAS: 215653-45-5
• 化学式: C₁₆H₂₀O₆S
• 分子量: 340.397
• InChiKey: ACRNVVSOJAUAEU-AVBIWOEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  63.22
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 3-O-acetyl-4,6-O-benzylidene-2-thio-α-D-mannopyranoside 在 三乙基硅基三氟甲磺酸酯 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 Acetic acid (2R,3S,4S,5S,6R)-4,5-diacetoxy-2-((2S,3S,4S,5R,6R)-4-acetoxy-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-ylsulfanyl)-6-acetoxymethyl-tetrahydro-thiopyran-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2)-alpha-D-Man-OMe in which the ring and/or glycosidic oxygen atoms have been replaced by sulfur have been synthesized as potential inhibitors of Class I mannosidase enzymes.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：

  methyl 3-O-acetyl-2-S-acetyl-4,6-O-benzylidene-2-thio-α-D-mannopyranoside 在 一水合肼 作用下， 以 吡啶 为溶剂， 反应 2.0h， 以82%的产率得到methyl 3-O-acetyl-4,6-O-benzylidene-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2)-alpha-D-Man-OMe in which the ring and/or glycosidic oxygen atoms have been replaced by sulfur have been synthesized as potential inhibitors of Class I mannosidase enzymes.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