Benzoic acid (2S,3R,4R,5S,6S)-2-bromomethyl-4-methanesulfonyloxy-5,6-dimethoxy-tetrahydro-pyran-3-yl ester | 183001-82-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Benzoic acid (2S,3R,4R,5S,6S)-2-bromomethyl-4-methanesulfonyloxy-5,6-dimethoxy-tetrahydro-pyran-3-yl ester
• CAS: 183001-82-3
• 化学式: C₁₆H₂₁BrO₈S
• 分子量: 453.308
• InChiKey: XISDXYDTKMRNRB-FAHYXWLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.34
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Benzoic acid (2S,3R,4R,5S,6S)-2-bromomethyl-4-methanesulfonyloxy-5,6-dimethoxy-tetrahydro-pyran-3-yl ester 在 potassium tert-butylate 、 sodium methylate 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 78.0h， 生成 (E)-(R)-4-((2R,3R,4S)-3-Benzyloxy-4-hydroxy-tetrahydro-thiophen-2-yl)-4-methoxy-but-2-enoic acid methyl ester
  参考文献：
  名称：

  Enantiospecific synthesis of 8-O-methylthioswainsonine from a derivative of D-glucose

  摘要：

  The thioanalogue 1, (1R,2S,4S,8R,8 alpha S)-1,2,8-trihydroxy-8-O-methylthioindolizidine of 8-O-methylswainsonine 2 has been enantiospecifically synthesized from the important key intermediate methyl 2-O-methyl-3,6-thioanhydro-alpha-D-mannopyranoside 7, in five steps. Formation of the bicyclic system in 1 took place with a high stereoselectivity. Compound 7 was obtained in eight steps from the readily available methyl alpha-D-glucopyranoside. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00330-8
• 作为产物：
  描述：

  methyl 4,6-O-benzylidene-3-O-methanesulfonyl-2-O-methyl-α-D-altropyranoside 在 N-溴代丁二酰亚胺(NBS) 、 barium carbonate 作用下， 以 四氯化碳 为溶剂， 反应 2.0h， 以80%的产率得到Benzoic acid (2S,3R,4R,5S,6S)-2-bromomethyl-4-methanesulfonyloxy-5,6-dimethoxy-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Enantiospecific synthesis of 8-O-methylthioswainsonine from a derivative of D-glucose

  摘要：

  The thioanalogue 1, (1R,2S,4S,8R,8 alpha S)-1,2,8-trihydroxy-8-O-methylthioindolizidine of 8-O-methylswainsonine 2 has been enantiospecifically synthesized from the important key intermediate methyl 2-O-methyl-3,6-thioanhydro-alpha-D-mannopyranoside 7, in five steps. Formation of the bicyclic system in 1 took place with a high stereoselectivity. Compound 7 was obtained in eight steps from the readily available methyl alpha-D-glucopyranoside. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00330-8