1,4-anhydro-2,3,5,6-tetra-O-benzyl-4-thio-D-galactitol | 672310-88-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,4-anhydro-2,3,5,6-tetra-O-benzyl-4-thio-D-galactitol
• 英文别名: (2S,3R,4R)-2-[(1R)-1,2-bis(phenylmethoxy)ethyl]-3,4-bis(phenylmethoxy)thiolane
• CAS: 672310-88-2
• 化学式: C₃₄H₃₆O₄S
• 分子量: 540.723
• InChiKey: CHNNOVSOFAOXQA-ITHRCTNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  39
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  62.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,4-anhydro-2,3,5,6-tetra-O-benzyl-4-thio-D-galactitol 在 palladium dihydroxide 六氟异丙醇 、 氢气 、 potassium carbonate 作用下， 以 水 、 溶剂黄146 为溶剂， 20.0~70.0 ℃ 、827.37 kPa 条件下， 反应 72.0h， 生成 1,4-anhydro-4-[(R)-[(2S,3S)-2,4-dihydroxy-3-(sulfooxy)butyl]sulfoniumylidene]-D-galactitol
  参考文献：
  名称：

  Synthesis of a novel class of sulfonium ions as potential inhibitors of UDP-galactopyranose mutase

  摘要：

  Two sulfonium salts of 1,4-anhydro-4-thio-D-galactitol, with structures related to the known sulfonium salt glycosidase inhibitor, salacinol, have been synthesized as potential inhibitors of UDP-galactopyranose mutase. The synthetic strategy relies on the alkylation reaction of 1,4-anhydro-2,3,5,6-tetra-O-benzyl-4-thin-D-galactitol at the sulfur atom with 2,4-O-benzylidene-D- or -L-erythritol-1,3-cyclic sulfate. In each case, the reaction proceeded stereoselectively to yield only one stereoisomer at the stereogenic sulfur atom. The effect of the polar solvent, 1,1,1,3,3,3-hexafluoroisopropanol (HFIP), in promoting high-yielding reactions is highlighted. The target compounds are then obtained by hydrogenolysis. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2003.09.036
• 作为产物：
  描述：

  1,2,3,4,5-penta-O-acetyl-α-D-galactofuranose 在 三乙基硅烷 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 24.0h， 生成 1,4-anhydro-2,3,5,6-tetra-O-benzyl-4-thio-D-galactitol
  参考文献：
  名称：

  Synthesis of a novel class of sulfonium ions as potential inhibitors of UDP-galactopyranose mutase

  摘要：

  Two sulfonium salts of 1,4-anhydro-4-thio-D-galactitol, with structures related to the known sulfonium salt glycosidase inhibitor, salacinol, have been synthesized as potential inhibitors of UDP-galactopyranose mutase. The synthetic strategy relies on the alkylation reaction of 1,4-anhydro-2,3,5,6-tetra-O-benzyl-4-thin-D-galactitol at the sulfur atom with 2,4-O-benzylidene-D- or -L-erythritol-1,3-cyclic sulfate. In each case, the reaction proceeded stereoselectively to yield only one stereoisomer at the stereogenic sulfur atom. The effect of the polar solvent, 1,1,1,3,3,3-hexafluoroisopropanol (HFIP), in promoting high-yielding reactions is highlighted. The target compounds are then obtained by hydrogenolysis. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2003.09.036