(2S,4aR,5R,6R,7S,8S,8aS)-5,6,8-Tris-benzyloxy-2-phenyl-hexahydro-benzo[1,3]dioxin-7-ol | 158883-07-9

• 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: (2S,4aR,5R,6R,7S,8S,8aS)-5,6,8-Tris-benzyloxy-2-phenyl-hexahydro-benzo[1,3]dioxin-7-ol
• 英文别名: (2S,4aR,5R,6R,7S,8S,8aS)-2-phenyl-5,6,8-tris(phenylmethoxy)-4a,5,6,7,8,8a-hexahydro-4H-benzo[d][1,3]dioxin-7-ol
• CAS: 158883-07-9
• 化学式: C₃₅H₃₆O₆
• 分子量: 552.667
• InChiKey: PSPAHOLLBXCYNL-MCOAYWBUSA-N

物化性质

• 沸点：
  691.3±55.0 °C(predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,4aR,5R,6R,7S,8S,8aS)-5,6,8-Tris-benzyloxy-2-phenyl-hexahydro-benzo[1,3]dioxin-7-ol 在 dimethyl sulfide borane 、 sodium cyanoborohydride 、 戴斯-马丁氧化剂 作用下， 生成 (1S,2R,3S,4S,5R,6S)-2,3,4,5-tetrakis(benzyloxy)-6-[(benzyloxy)methyl]cyclohexanol
  参考文献：
  名称：

  A Divergent Route for a Total Synthesis of Cyclophellitol and Epicyclophellitol from a [2.2.2]Oxabicyclic Glycoside Prepared from D-Glucal

  摘要：

  D-Glucal has been used for syntheses of Tatsuta's penultimate intermediate for cyclophellitol and epicyclophellitol via a 6-exo-trig radical cyclization of 2-deoxy-2-iodo-6-alkynyl glycoside, the diastereomeric mixture produced thereby being separated into two sets, each of which leads to one or other target materials.

  DOI：

  10.1021/jo00091a004
• 作为产物：
  描述：

  (1R,2R,3R,4R,6R)-2,3,6-Tris-benzyloxy-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-[1-phenyl-meth-(Z)-ylidene]-cyclohexanol 在 盐酸 、 三乙酰氧基硼氢化钠 、 臭氧 、 三苯基膦 作用下， 反应 3.0h， 生成 (2S,4aR,5R,6R,7S,8S,8aS)-5,6,8-Tris-benzyloxy-2-phenyl-hexahydro-benzo[1,3]dioxin-7-ol
  参考文献：
  名称：

  A Divergent Route for a Total Synthesis of Cyclophellitol and Epicyclophellitol from a [2.2.2]Oxabicyclic Glycoside Prepared from D-Glucal

  摘要：

  D-Glucal has been used for syntheses of Tatsuta's penultimate intermediate for cyclophellitol and epicyclophellitol via a 6-exo-trig radical cyclization of 2-deoxy-2-iodo-6-alkynyl glycoside, the diastereomeric mixture produced thereby being separated into two sets, each of which leads to one or other target materials.

  DOI：

  10.1021/jo00091a004