(1S,2S,4R,5R)-4-hydroxy-1-methyl-6-oxa-bicyclo[3.1.0]hexane-2-carboxylic acid ethyl ester | 524011-37-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (1S,2S,4R,5R)-4-hydroxy-1-methyl-6-oxa-bicyclo[3.1.0]hexane-2-carboxylic acid ethyl ester
• 英文别名: ethyl (1S,2S,4R,5R)-4-hydroxy-1-methyl-6-oxabicyclo[3.1.0]hexane-2-carboxylate
• CAS: 524011-37-8
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: MPGVPZXTMMHSEC-PULFBKJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2S,4R,5R)-4-hydroxy-1-methyl-6-oxa-bicyclo[3.1.0]hexane-2-carboxylic acid ethyl ester 在 Rhysomucor meihei lipase lithium aluminium tetrahydride 、 偶氮二甲酸二异丙酯 、 氨 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 28.0h， 生成 ((1S,2R,4R,5R)-4-(6-(cyclopropylamino)-9H-purin-9-yl)-1-methyl-6-oxa-bicyclo[3.1.0]hex-2-yl)methanol
  参考文献：
  名称：

  Chemoenzymatic synthesis of novel adenosine carbanucleoside analogues containing a locked 3′-methyl-2′,3′-β-oxirane-fused system

  摘要：

  Starting from a readily available enantiopure building block, a straightforward enantioselective approach to 3 '-methyl-2 ',3 '- beta-oxirane-fused carbanucleosides bearing adenosine analogues is detailed. The key steps in the syntheses involved a lipase-catalyzed regioseleclive monoacylation of a diol to obtain the key intermediate and direct coupling of this key intermediate with diversely substituted purine nucleobases under Mitsunobu reaction conditions providing only the N-9 target molecules. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.122
• 作为产物：
  描述：

  ethyl cis-4-hydroxy-2-methylcyclopent-2-ene-1-carboxylate 在 bis(acetylacetonate)oxovanadium 叔丁基过氧化氢 作用下， 以 苯 为溶剂， 反应 20.0h， 以98%的产率得到(1S,2S,4R,5R)-4-hydroxy-1-methyl-6-oxa-bicyclo[3.1.0]hexane-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Enantioselective Synthesis of 3-Methylcarbapentofuranose Derivatives, Based on a Chemoenzymatic Procedure

  摘要：

  The enantioselective synthesis of 3-methylcarbapentofuranose derivatives through the use of a racemic substituted cyclopentenylcarboxylate as the carbon building block and a number of stereoselective transformations is described. All of the stereogenic centres of these derivatives are directed by the two stereogenic centres created early in the key cyclopentene moiety by a lipase-catalysed enantioselective acetylation.

  DOI：

  10.1002/1099-0690(200301)2003:1<92::aid-ejoc92>3.0.co;2-v