methyl (2R,3R,4R,5R,6R)-4-benzoyloxy-3-bromo-2-hydroxy-5,6-bis(phenylmethoxy)oxane-2-carboxylate | 219864-86-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2R,3R,4R,5R,6R)-4-benzoyloxy-3-bromo-2-hydroxy-5,6-bis(phenylmethoxy)oxane-2-carboxylate
• CAS: 219864-86-5
• 化学式: C₂₈H₂₇BrO₈
• 分子量: 571.422
• InChiKey: KJRBBSIMPZRSND-DUSVHXPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (2R,3R,4R,5R,6R)-4-benzoyloxy-3-bromo-2-hydroxy-5,6-bis(phenylmethoxy)oxane-2-carboxylate 在 三正丁基氢锡 、 溴化钛(IV) 、 silver(l) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 16.0h， 生成 methyl (2S,3S,4S,5R,6R)-4-benzoyloxy-3-hydroxy-5,6-bis(phenylmethoxy)oxane-2-carboxylate
  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：

  (2S,3S,4S,5R,6R)-5,6-Bis-benzyloxy-3,4-dihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 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 、 水 为溶剂， 反应 20.0h， 生成 methyl (2R,3R,4R,5R,6R)-4-benzoyloxy-3-bromo-2-hydroxy-5,6-bis(phenylmethoxy)oxane-2-carboxylate
  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.