methyl 2,4-di-O-benzoyl-6-bromo-6-deoxy-3-O-methanesulfonyl-α-D-glucopyranoside | 169048-74-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,4-di-O-benzoyl-6-bromo-6-deoxy-3-O-methanesulfonyl-α-D-glucopyranoside
• 英文别名: [(2S,3R,4S,5R,6S)-5-benzoyloxy-2-(bromomethyl)-6-methoxy-4-methylsulfonyloxyoxan-3-yl] benzoate
• CAS: 169048-74-2
• 化学式: C₂₂H₂₃BrO₉S
• 分子量: 543.389
• InChiKey: SRZDVOLKRCWLKZ-MRSOFBGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 2,4-di-O-benzoyl-6-bromo-6-deoxy-3-O-methanesulfonyl-α-D-glucopyranoside 在 sodium methylate 、 镍 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 3.83h， 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 为溶剂， 反应 24.5h， 生成 methyl 2,4-di-O-benzoyl-6-bromo-6-deoxy-3-O-methanesulfonyl-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

• 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).