2,3,4-tri-O-benzoyl-1,6-thioanhydro-β-D-mannose | 910221-00-0

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2,3,4-tri-O-benzoyl-1,6-thioanhydro-β-D-mannose
• CAS: 910221-00-0
• 化学式: C₂₇H₂₂O₇S
• 分子量: 490.533
• InChiKey: SRUORGYHDIMOKI-KZRLHFJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  35.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  88.13
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzoyl-1,6-thioanhydro-β-D-mannose 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以99%的产率得到(-)-1,6-dideoxy-1,6-thioanhydro-D-mannopyranose
  参考文献：
  名称：

  Conformationally locked thiosugars as potent α-mannosidase inhibitors: Synthesis, biochemical and docking studies

  摘要：

  series of thiosugar derivatives (thiolevomannosans) derived from mannose were synthesized and their inhibitory activity was tested against alpha-mannosidase (jack bean). These inhibitors were found to be more potent than the well-known inhibitors like kifunensine and deoxymannojirimycin based on docking and biochemical studies. The sulfone derivative 10 was shown to be the best inhibitor of alpha-mannosidase with the K-i value of 350 nM. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.06.011
• 作为产物：
  描述：

  (3S,4S,5R,6R)-6-((tosyloxy)methyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetrabenzoate 在 benzyltriethylammonium tetrathiomolybdate 、 氢溴酸 作用下， 以 溶剂黄146 、 乙腈 为溶剂， 反应 4.0h， 生成 2,3,4-tri-O-benzoyl-1,6-thioanhydro-β-D-mannose
  参考文献：
  名称：

  New conformationally locked thioderivatives of mannose: synthesis, applications, and mechanistic studies

  摘要：

  Tetrathiomolybdate has been used as an efficient sulfur-transfer reagent in the synthesis of a number of thiolevomannosan derivatives having an axial-rich C-1(4) conformation. An unprecedented synthesis of a novel thioorthoester and its synthetic utility in glycosylation has been demonstrated. This is a general and efficient method for the synthesis of conformationally locked thiosugars. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.06.001