methyl (1S,2R 3R,4S)-2,3,4-trihydroxy-cyclohex-5-ene-1-carboxylate | 1237596-86-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (1S,2R 3R,4S)-2,3,4-trihydroxy-cyclohex-5-ene-1-carboxylate
• 英文别名: (1S,4S,5R,6R)-methyl 4,5,6-trihydroxycyclohex-2-enecarboxylate；methyl (1S,4S,5R,6R)-4,5,6-trihydroxycyclohex-2-ene-1-carboxylate
• CAS: 1237596-86-9
• 化学式: C₈H₁₂O₅
• 分子量: 188.18
• InChiKey: WVBNVUDAOUVDAV-VWDOSNQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (1S,2R 3R,4S)-2,3,4-trihydroxy-cyclohex-5-ene-1-carboxylate 在 sodium tetrahydroborate 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.5h， 以96%的产率得到DL-(1,3/2,4)-4-(hydroxymethyl)-5-cyclohexene-1,2,3-triol
  参考文献：
  名称：

  Synthesis of novel cyano-cyclitols and their stereoselective biotransformation catalyzed by Rhodococcus erythropolis A4

  摘要：

  A variety of novel cyano-cyclitols possessing complex stereochemistry have been synthesized. These compounds were subjected to the biocatalyzed hydrolysis of their nitrile groups. The bacterial strain Rhodococcus erythropolis A4, expressing a nitrile hydratase/amidase bienzymatic system, was able to recognize (1R,25,35,4R)/(15,2R,3R,4.5)-1-cyano-2,3,4-trihydroxy-cyclohex-5-ene and trans-3-cyanocyclohexa-3,5-diene-1,2-diol, and to catalyze their transformations into the corresponding amides and acids. The kinetic and stereochemical trends of these biotransformations, a rare example of the enantiorecognition of a rigid bulky aliphatic substrate, are discussed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.022
• 作为产物：
  描述：

  甲醇 、 (+)-(1S,2R,3R,4S)-2,3,4-trihydroxy-cyclohex-5-ene-1-carboxylic acid 在 盐酸 作用下， 以 水 为溶剂， 反应 8.0h， 以76%的产率得到methyl (1S,2R 3R,4S)-2,3,4-trihydroxy-cyclohex-5-ene-1-carboxylate
  参考文献：
  名称：

  Synthesis of novel cyano-cyclitols and their stereoselective biotransformation catalyzed by Rhodococcus erythropolis A4

  摘要：

  A variety of novel cyano-cyclitols possessing complex stereochemistry have been synthesized. These compounds were subjected to the biocatalyzed hydrolysis of their nitrile groups. The bacterial strain Rhodococcus erythropolis A4, expressing a nitrile hydratase/amidase bienzymatic system, was able to recognize (1R,25,35,4R)/(15,2R,3R,4.5)-1-cyano-2,3,4-trihydroxy-cyclohex-5-ene and trans-3-cyanocyclohexa-3,5-diene-1,2-diol, and to catalyze their transformations into the corresponding amides and acids. The kinetic and stereochemical trends of these biotransformations, a rare example of the enantiorecognition of a rigid bulky aliphatic substrate, are discussed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.022

文献信息

• A novel chemo-multienzymatic synthesis of bioactive cyclophellitol and epi-cyclophellitol in both enantiopure forms
  作者：Nicola D’Antona、Raffaele Morrone、Paolo Bovicelli、Giovanni Gambera、David Kubáč、Ludmila Martínková

  DOI：10.1016/j.tetasy.2010.10.010

  日期：2010.10

  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