(2R,3S,4S,5R,6R)-4,5-Bis-benzoyloxy-6-benzyloxy-2-bromo-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester | 219865-11-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4S,5R,6R)-4,5-Bis-benzoyloxy-6-benzyloxy-2-bromo-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester
• 英文别名: methyl (2R,3S,4S,5R,6R)-4,5-dibenzoyloxy-2-bromo-3-hydroxy-6-phenylmethoxyoxane-2-carboxylate
• CAS: 219865-11-9
• 化学式: C₂₈H₂₅BrO₉
• 分子量: 585.405
• InChiKey: VVGYMEZLLXJBOK-AXUPOTPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 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,3S,4S,5R,6R)-4,5-Bis-benzoyloxy-6-benzyloxy-2-bromo-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester 在 吡啶 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 1.5h， 生成 (2S,3S,4S,5R,6R)-3-Acetoxy-4,5-bis-benzoyloxy-6-benzyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Regio- and Stereoselective Synthesis of β-d-Gluco-, α-l-Ido-, and α-l-Altropyranosiduronic Acids from Δ⁴-Uronates

  摘要：

  The stereoselective synthesis of beta-D-glucopyranosiduronic, alpha-L-idopyranosiduronic, and alpha-L-altropyranosiduronic acids has been performed from different Delta(4)-uronate monosaccharides. Bromination of the C-4,5 double bond provided the trans-diaxial bromohydrin derivatives, which were converted to the corresponding epoxides in high yields. Direct reduction of the epoxides using boranetetrahydrofuran complex led to the corresponding glucuronic acids in low to good yields. Glucuronic acids were also obtained in satisfactory yields through a two-steps procedure involving bromination of the epoxide with titanium(IV) bromide followed by reduction using tributyltin hydride. Lewis acid-catalyzed rearrangement of these epoxides led to the corresponding alpha-L C-4 ketopyranosides adopting the C-1(4) chair conformation. Hydride reduction afforded the alpha-L-idopyranosiduronic or the alpha-L-altropyranosiduronic acids, the stereoselectivity of the reduction being controlled by the appropriate substitution pattern.

  DOI：

  10.1021/jo981477k
• 作为产物：
  描述：

  (1S,3R,4R,5R,6S)-4,5-Bis-benzoyloxy-3-benzyloxy-2,7-dioxa-bicyclo[4.1.0]heptane-1-carboxylic acid methyl ester 在 溴化钛(IV) 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以26%的产率得到(2R,3S,4S,5R,6R)-4,5-Bis-benzoyloxy-6-benzyloxy-2-bromo-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Regio- and Stereoselective Synthesis of β-d-Gluco-, α-l-Ido-, and α-l-Altropyranosiduronic Acids from Δ⁴-Uronates

  摘要：

  The stereoselective synthesis of beta-D-glucopyranosiduronic, alpha-L-idopyranosiduronic, and alpha-L-altropyranosiduronic acids has been performed from different Delta(4)-uronate monosaccharides. Bromination of the C-4,5 double bond provided the trans-diaxial bromohydrin derivatives, which were converted to the corresponding epoxides in high yields. Direct reduction of the epoxides using boranetetrahydrofuran complex led to the corresponding glucuronic acids in low to good yields. Glucuronic acids were also obtained in satisfactory yields through a two-steps procedure involving bromination of the epoxide with titanium(IV) bromide followed by reduction using tributyltin hydride. Lewis acid-catalyzed rearrangement of these epoxides led to the corresponding alpha-L C-4 ketopyranosides adopting the C-1(4) chair conformation. Hydride reduction afforded the alpha-L-idopyranosiduronic or the alpha-L-altropyranosiduronic acids, the stereoselectivity of the reduction being controlled by the appropriate substitution pattern.

  DOI：

  10.1021/jo981477k

文献信息

• Regio- and Stereoselective Synthesis of β-<scp>d</scp>-Gluco-, α-<scp>l</scp>-Ido-, and α-<scp>l</scp>-Altropyranosiduronic Acids from Δ⁴-Uronates
  作者：Hélène G. Bazin、Michael W. Wolff、Robert J. Linhardt

  DOI：10.1021/jo981477k

  日期：1999.1.1

  The stereoselective synthesis of beta-D-glucopyranosiduronic, alpha-L-idopyranosiduronic, and alpha-L-altropyranosiduronic acids has been performed from different Delta(4)-uronate monosaccharides. Bromination of the C-4,5 double bond provided the trans-diaxial bromohydrin derivatives, which were converted to the corresponding epoxides in high yields. Direct reduction of the epoxides using boranetetrahydrofuran complex led to the corresponding glucuronic acids in low to good yields. Glucuronic acids were also obtained in satisfactory yields through a two-steps procedure involving bromination of the epoxide with titanium(IV) bromide followed by reduction using tributyltin hydride. Lewis acid-catalyzed rearrangement of these epoxides led to the corresponding alpha-L C-4 ketopyranosides adopting the C-1(4) chair conformation. Hydride reduction afforded the alpha-L-idopyranosiduronic or the alpha-L-altropyranosiduronic acids, the stereoselectivity of the reduction being controlled by the appropriate substitution pattern.