(2R,3aS,4R,5R,6S,7R,7aR)-5,6,7-tris(benzyloxy)-2-phenylhexahydrobenzo[d][1,3]dioxol-4-ol | 1185996-00-2

• 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: (2R,3aS,4R,5R,6S,7R,7aR)-5,6,7-tris(benzyloxy)-2-phenylhexahydrobenzo[d][1,3]dioxol-4-ol
• CAS: 1185996-00-2
• 化学式: C₃₄H₃₄O₆
• 分子量: 538.64
• InChiKey: IJHTUCVWMLHEQS-VEQOTMKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  40.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2R,3aS,4R,5R,6S,7R,7aR)-5,6,7-tris(benzyloxy)-2-phenylhexahydrobenzo[d][1,3]dioxol-4-ol 、 3-溴丙烯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以80%的产率得到
  参考文献：
  名称：

  Efficient syntheses of chiral myo-inositol derivatives—key intermediates in glycosylphosphatidylinositol (GPI) syntheses

  摘要：

  A facile and effective method was developed for large-scale syntheses of myo-inositol derivatives with the 1,2,6-O-positions differentiated from each other and from other positions as well. The syntheses started from methyl alpha-D-glucopyranoside, and the key steps are Ferrier rearrangement and a series of other regioselective and stereoselective reactions. The target compounds are key intermediates in the synthesis of GPIs. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.151
• 作为产物：
  描述：

  苯甲醛二甲缩醛 、 3,4,5-tri-O-benzyl-D-myo-inositol 在 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 生成 (2R,3aS,4R,5R,6S,7R,7aR)-5,6,7-tris(benzyloxy)-2-phenylhexahydrobenzo[d][1,3]dioxol-4-ol 、 (2S,3aS,4R,5R,6S,7R,7aR)-5,6,7-tris(benzyloxy)-2-phenylhexahydrobenzo[d][1,3]dioxol-4-ol
  参考文献：
  名称：

  Efficient syntheses of chiral myo-inositol derivatives—key intermediates in glycosylphosphatidylinositol (GPI) syntheses

  摘要：

  A facile and effective method was developed for large-scale syntheses of myo-inositol derivatives with the 1,2,6-O-positions differentiated from each other and from other positions as well. The syntheses started from methyl alpha-D-glucopyranoside, and the key steps are Ferrier rearrangement and a series of other regioselective and stereoselective reactions. The target compounds are key intermediates in the synthesis of GPIs. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.151