methyl 6-S-acetyl-2,4-di-O-benzoyl-6-deoxy-3-O-methanesulfonyl-6-thio-α-D-glucopyranoside | 169048-75-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-S-acetyl-2,4-di-O-benzoyl-6-deoxy-3-O-methanesulfonyl-6-thio-α-D-glucopyranoside
• 英文别名: methyl-6-S-acetyl-2,4-di-O-benzoyl-3-O-methanesulfonyl-6-thio-α-D-glucopyranoside；[(2S,3R,4S,5R,6S)-2-(acetylsulfanylmethyl)-5-benzoyloxy-6-methoxy-4-methylsulfonyloxyoxan-3-yl] benzoate
• CAS: 169048-75-3
• 化学式: C₂₄H₂₆O₁₀S₂
• 分子量: 538.596
• InChiKey: VIMHSGXSRBZQTN-IDYLKPADSA-N

物化性质

• 沸点：
  685.4±55.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  165
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl 6-S-acetyl-2,4-di-O-benzoyl-6-deoxy-3-O-methanesulfonyl-6-thio-α-D-glucopyranoside 在 sodium methylate 、 镍 作用下， 以 甲醇 、 乙醇 、 苯 为溶剂， 反应 2.33h， 生成 (2S,3R,5S,6R)-2-甲氧基-6-甲基四氢吡喃-3,5-二醇
  参考文献：
  名称：

  3,6-Thioanhydro sugars as important key intermediates in the enantiospecific synthesis of chiral polyhydroxythiolanes

  摘要：

  Methyl 3,6-thioanhydro-alpha-D-glucopyranoside (5) was obtained in seven steps from the commercially available methyl alpha-D-glucopyranoside. Transformation of 5 into (2R,3R,4S)-3,4-dihydroxy-2-[(S)-1,2-dihydroxyethyl]th (9) was achieved by acid hydrolysis and subsequent reduction without isolation of its formyl derivative (8).

  DOI：

  10.1016/0957-4166(95)00137-e
• 作为产物：
  描述：

  methyl 2-O-benzoyl-4,6-di-O-benzylidene-α-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 barium carbonate 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 methyl 6-S-acetyl-2,4-di-O-benzoyl-6-deoxy-3-O-methanesulfonyl-6-thio-α-D-glucopyranoside
  参考文献：
  名称：

  3,6-Thioanhydro sugars as important key intermediates in the enantiospecific synthesis of chiral polyhydroxythiolanes

  摘要：

  Methyl 3,6-thioanhydro-alpha-D-glucopyranoside (5) was obtained in seven steps from the commercially available methyl alpha-D-glucopyranoside. Transformation of 5 into (2R,3R,4S)-3,4-dihydroxy-2-[(S)-1,2-dihydroxyethyl]th (9) was achieved by acid hydrolysis and subsequent reduction without isolation of its formyl derivative (8).

  DOI：

  10.1016/0957-4166(95)00137-e

文献信息

• Synthesis of 4-substituted phenyl 3,6-anhydro-1,3-dithio-d-glucofuranosides and -pyranosides as well as 2,6-anhydro-1,2-dithio-α-d-altrofuranosides possessing antithrombotic activity
  作者：Éva Bozó、Sándor Boros、János Kuszmann

  DOI：10.1016/s0008-6215(00)00218-4

  日期：2000.11

  altrofuranose (40). Glycosidation of 4-cyanobenzethiol with 32alpha in the presence of trimethylsilyl triflate as promoter afforded 4-cyanophenyl 3,6-anhydro-2,4-di-O-(4-nitrobenzoyl)-1,3-dithio-beta-D-glucopyranoside as a minor component only, besides 4-cyanophenyl 3,6-anhydro-2-S-(4-cyanophenyl)-4-O-(4-nitrobenzoyl)-1,2,3-trithio-beta-D-glucopyranoside. When boron trifluoride etherate was used as

  从D-葡萄糖开始合成1,2,5-Tri-O-乙酰基-3,6-脱水-3-硫代-D-葡萄糖呋喃糖，并用作4-氰基和4-硝基苯硫醇糖基化的供体。在后一反应中，除了4-硝基苯基2,5-二-O-乙酰基-3,6-脱水-1,3-二硫代-D-葡糖呋喃糖苷的异头混合物外，相应的2,6-脱水-1，还获得了通过糖部分的重排形成的2-二硫代-D-呋喃呋喃糖苷。在三氟乙酸水溶液水解甲基3,6-脱水-2,4-二-O-（4-硝基苯甲酰基）-3-硫代-α-D-吡喃葡萄糖苷的糖苷键期间，可以观察到类似的重排，得到除1-O-乙酰基-3,6-脱水-2,4-二-O-（4-硝基苯甲酰基）-3-硫代-α-D-吡喃葡萄糖（32alpha），1,1,5-三- O-乙酰基-3,6-脱水-2,4-二-O-（4-硝基苯甲酰基）-3-硫代-D-葡萄糖，甲基3,6-脱水-2，4-二-O-（4-硝基苯甲酰基）-3-硫代β-D-吡喃葡萄糖苷和1,5-二-O-乙酰基-2
• 3,6-Thioanhydro sugars as important key intermediates in the enantiospecific synthesis of chiral polyhydroxythiolanes
  作者：Isidoro Izquierdo、Maria T. Plaza、Rafael Asenjo、Miguel Rodríguez

  DOI：10.1016/0957-4166(95)00137-e

  日期：1995.5

  Methyl 3,6-thioanhydro-alpha-D-glucopyranoside (5) was obtained in seven steps from the commercially available methyl alpha-D-glucopyranoside. Transformation of 5 into (2R,3R,4S)-3,4-dihydroxy-2-[(S)-1,2-dihydroxyethyl]th (9) was achieved by acid hydrolysis and subsequent reduction without isolation of its formyl derivative (8).