((1S,2R,3S,4S,5S,6R)-2,3,4-Tris-benzyloxy-5,6-dihydroxy-cyclohexyl)-acetic acid | 215303-33-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ((1S,2R,3S,4S,5S,6R)-2,3,4-Tris-benzyloxy-5,6-dihydroxy-cyclohexyl)-acetic acid
• 英文别名: 2-[(1S,2R,3S,4S,5S,6R)-2,3-dihydroxy-4,5,6-tris(phenylmethoxy)cyclohexyl]acetic acid
• CAS: 215303-33-6
• 化学式: C₂₉H₃₂O₇
• 分子量: 492.569
• InChiKey: ISZVNEQYFVAUMK-STVFCJJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ((1S,2R,3S,4S,5S,6R)-2,3,4-Tris-benzyloxy-5,6-dihydroxy-cyclohexyl)-acetic acid 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 ((1R,2R,3S,4R,5S,6R)-2,3-Diacetoxy-4,5,6-tris-benzyloxy-cyclohexyl)-acetic acid methyl ester
  参考文献：
  名称：

  Free Radical Studies and Solutions to the Synthesis of (+)-Cyclophellitol

  摘要：

  D-Xylose serves as a starting material for approaches to the synthesis of the glucosidase inhibitors, (+)-cyclophellitol (1) and (+)-epi-cyclophellitol (2). An investigation of the cyclization of diastereomeric oxiranyl radicals to achieve this goal was moderately successful with the diastereomer that would have led to epi-cyclophellitol undergoing cyclization. An alternative route to cyclophellitol from D-xylose employed Grubbs' ring closure metathesis and radical transformations to complete the synthesis.

  DOI：

  10.1021/jo981211d
• 作为产物：
  描述：

  methyl 2-[(1S,2R,3R,4S,5R,6S)-3,4,5-tris(phenylmethoxy)-7-oxabicyclo[4.1.0]heptan-2-yl]acetate 在 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 20.0h， 以78%的产率得到((1S,2R,3S,4S,5S,6R)-2,3,4-Tris-benzyloxy-5,6-dihydroxy-cyclohexyl)-acetic acid
  参考文献：
  名称：

  Free Radical Studies and Solutions to the Synthesis of (+)-Cyclophellitol

  摘要：

  D-Xylose serves as a starting material for approaches to the synthesis of the glucosidase inhibitors, (+)-cyclophellitol (1) and (+)-epi-cyclophellitol (2). An investigation of the cyclization of diastereomeric oxiranyl radicals to achieve this goal was moderately successful with the diastereomer that would have led to epi-cyclophellitol undergoing cyclization. An alternative route to cyclophellitol from D-xylose employed Grubbs' ring closure metathesis and radical transformations to complete the synthesis.

  DOI：

  10.1021/jo981211d