(2S,3S)-diacetoxy-(1R,4R)-dihydroxycyclohex-5-ene | 252316-80-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3S)-diacetoxy-(1R,4R)-dihydroxycyclohex-5-ene
• 英文别名: [(1S,2R,5R,6S)-6-acetyloxy-2,5-dihydroxycyclohex-3-en-1-yl] acetate
• CAS: 252316-80-6
• 化学式: C₁₀H₁₄O₆
• 分子量: 230.218
• InChiKey: VHJZBUHIWOSLME-IMSYWVGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3S)-diacetoxy-(1R,4R)-dihydroxycyclohex-5-ene 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 以100%的产率得到(1R,2S,3S,4R)-1,2,3,4,tetrahydroxy-5-cyclohexene
  参考文献：
  名称：

  Enzymatic resolution of (±)-conduritol-B, a key intermediate for the synthesis of glycosidase inhibitors

  摘要：

  Lipases from porcine pancreas, Candida cylindracea and Mucor miehei (adsorbed on support, Lipozyme(R) IM) catalysed in t-butylmethylether the alcoholysis of rac-conduritol-B peracetate, (+/-)-1, by n-butanol to give enantiopure (2S,3S)-diacetoxy-(1R,4R)-dihydroxycyclohex-5-ene, (-)-3, and (1S,2R,3R,4S)-tetraacetoxy-cyclohex-5-ene, (+)-1. The enantioforms (+)- and (-)-conduritol-B, obtained after chemical hydrolysis of (-)-3 and (+)-1, respectively, may be employed to prepare both the enantiomers of conduritol-B epoxide and cyclophellitol, powerful inhibitors of glycosidases. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00344-4
• 作为产物：
  描述：

  牛弥菜醇B四乙酸酯 在 lipozyme 、 正丁醇 作用下， 以 various solvent(s) 为溶剂， 反应 24.0h， 以44%的产率得到(2S,3S)-diacetoxy-(1R,4R)-dihydroxycyclohex-5-ene
  参考文献：
  名称：

  Enzymatic resolution of (±)-conduritol-B, a key intermediate for the synthesis of glycosidase inhibitors

  摘要：

  Lipases from porcine pancreas, Candida cylindracea and Mucor miehei (adsorbed on support, Lipozyme(R) IM) catalysed in t-butylmethylether the alcoholysis of rac-conduritol-B peracetate, (+/-)-1, by n-butanol to give enantiopure (2S,3S)-diacetoxy-(1R,4R)-dihydroxycyclohex-5-ene, (-)-3, and (1S,2R,3R,4S)-tetraacetoxy-cyclohex-5-ene, (+)-1. The enantioforms (+)- and (-)-conduritol-B, obtained after chemical hydrolysis of (-)-3 and (+)-1, respectively, may be employed to prepare both the enantiomers of conduritol-B epoxide and cyclophellitol, powerful inhibitors of glycosidases. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00344-4