(1S,3R,4R,5R,6S)-3-Benzyloxy-4,5-bis-(2,2-dimethyl-propionyloxy)-2,7-dioxa-bicyclo[4.1.0]heptane-1-carboxylic acid methyl ester | 188003-35-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3R,4R,5R,6S)-3-Benzyloxy-4,5-bis-(2,2-dimethyl-propionyloxy)-2,7-dioxa-bicyclo[4.1.0]heptane-1-carboxylic acid methyl ester
• CAS: 188003-35-2
• 化学式: C₂₄H₃₂O₉
• 分子量: 464.513
• InChiKey: DAOXGBRNCZULPG-CCSDNGFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.74
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  109.89
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (1S,3R,4R,5R,6S)-3-Benzyloxy-4,5-bis-(2,2-dimethyl-propionyloxy)-2,7-dioxa-bicyclo[4.1.0]heptane-1-carboxylic acid methyl ester 在 sodium tetrahydroborate 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 氘代氯仿 、 乙醇 为溶剂， 反应 1.0h， 生成 (2R,3S,4S,5R,6R)-6-Benzyloxy-4,5-bis-(2,2-dimethyl-propionyloxy)-3-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
• 作为产物：
  描述：

  (4S,5R,6R)-6-Benzyloxy-4,5-bis-(2,2-dimethyl-propionyloxy)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester 在 N-溴代丁二酰亚胺(NBS) 、 水 、 silver(l) oxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 (1S,3R,4R,5R,6S)-3-Benzyloxy-4,5-bis-(2,2-dimethyl-propionyloxy)-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