(1S,4S,5R,6R)-methyl 4,5,6-tris(benzyloxy)-cyclohex-2-enecarboxylate | 1261160-14-8

• 分子结构分类: 有机化合物
• 英文名称: (1S,4S,5R,6R)-methyl 4,5,6-tris(benzyloxy)-cyclohex-2-enecarboxylate
• CAS: 1261160-14-8
• 化学式: C₂₉H₃₀O₅
• 分子量: 458.554
• InChiKey: GUHXYUQKKJMGHN-YVHASNINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  34.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1S,4S,5R,6R)-methyl 4,5,6-tris(benzyloxy)-cyclohex-2-enecarboxylate 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.5h， 以96%的产率得到(1R,2R,5S,6S)-5,6-bis(benzyloxy)-2-{[(tert-butyldimethylsilyl)-oxy]methyl}cyclohex-3-en-1-ol
  参考文献：
  名称：

  A novel chemo-multienzymatic synthesis of bioactive cyclophellitol and epi-cyclophellitol in both enantiopure forms

  摘要：

  A new route to synthesize cyclophellitol and epi-cyclophellitol from racemic starting materials in enantiopure forms has been developed The synthesis involves a multi-enzymatic biotransformation pathway of the novel cyano-cyclitol (1R 4S 5R 6R)/(1S 4R 5S 6S)-4 5 6-trihydroxycyclohex-2-enecarbonitrile by a cooperative use of lipase nitrile hydratase and amidase (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2010.10.010
• 作为产物：
  描述：

  methyl (1S,2R 3R,4S)-2,3,4-trihydroxy-cyclohex-5-ene-1-carboxylate 、 溴甲苯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以98%的产率得到(1S,4S,5R,6R)-methyl 4,5,6-tris(benzyloxy)-cyclohex-2-enecarboxylate
  参考文献：
  名称：

  A novel chemo-multienzymatic synthesis of bioactive cyclophellitol and epi-cyclophellitol in both enantiopure forms

  摘要：

  A new route to synthesize cyclophellitol and epi-cyclophellitol from racemic starting materials in enantiopure forms has been developed The synthesis involves a multi-enzymatic biotransformation pathway of the novel cyano-cyclitol (1R 4S 5R 6R)/(1S 4R 5S 6S)-4 5 6-trihydroxycyclohex-2-enecarbonitrile by a cooperative use of lipase nitrile hydratase and amidase (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2010.10.010