(2R,3R,4R,5R,6R)-4,5-Diacetoxy-6-benzyloxy-3-bromo-2-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester | 188003-30-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4R,5R,6R)-4,5-Diacetoxy-6-benzyloxy-3-bromo-2-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester
• 英文别名: methyl (2R,3R,4R,5R,6R)-4,5-diacetyloxy-3-bromo-2-hydroxy-6-phenylmethoxyoxane-2-carboxylate
• CAS: 188003-30-7
• 化学式: C₁₈H₂₁BrO₉
• 分子量: 461.263
• InChiKey: HLZUAKALWRBEOB-HBPKQKSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R,6R)-4,5-Diacetoxy-6-benzyloxy-3-bromo-2-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 以15%的产率得到(1S,3R,4R,5R,6S)-4,5-Diacetoxy-3-benzyloxy-2,7-dioxa-bicyclo[4.1.0]heptane-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Regio and stereoselective conversion of Δ4-uronic acids to l-Ido- and d-glucopyranosiduronic acids

  摘要：

  Synthesis of L-ido- and D-glucopyranosiduronic acids was performed starting from protected Delta(4)-uronic acids 3a-f. Bromination of the C-4,5 double bond provided the trans-diaxial bromohydrin derivatives 6a-d, which were converted to the corresponding epoxides 7a-d in high yields. Direct reduction of these epoxides using borane-tetrahydrofuran complex afforded the o-glucopyranosiduronic acids 9b-d, while Lewis acid rearrangment through the C-4 keto intermediate 10b-d afforded the L-idopyranosiduronic acids 11b-d. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(96)02514-2
• 作为产物：
  描述：

  苄基beta-D-吡喃葡糖苷酸甲酯三乙酸酯 在 N-溴代丁二酰亚胺(NBS) 、 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 (2R,3R,4R,5R,6R)-4,5-Diacetoxy-6-benzyloxy-3-bromo-2-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Regio and stereoselective conversion of Δ4-uronic acids to l-Ido- and d-glucopyranosiduronic acids

  摘要：

  Synthesis of L-ido- and D-glucopyranosiduronic acids was performed starting from protected Delta(4)-uronic acids 3a-f. Bromination of the C-4,5 double bond provided the trans-diaxial bromohydrin derivatives 6a-d, which were converted to the corresponding epoxides 7a-d in high yields. Direct reduction of these epoxides using borane-tetrahydrofuran complex afforded the o-glucopyranosiduronic acids 9b-d, while Lewis acid rearrangment through the C-4 keto intermediate 10b-d afforded the L-idopyranosiduronic acids 11b-d. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(96)02514-2