acetic acid (1S,2R,4R,5R)-4-(6-chloro-9H-purin-9-yl)-1-methyl-6-oxa-bicyclo[3.1.0]hex-2-ylmethyl ester | 943222-40-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: acetic acid (1S,2R,4R,5R)-4-(6-chloro-9H-purin-9-yl)-1-methyl-6-oxa-bicyclo[3.1.0]hex-2-ylmethyl ester
• 英文别名: [(1S,2R,4R,5R)-4-(6-chloropurin-9-yl)-1-methyl-6-oxabicyclo[3.1.0]hexan-2-yl]methyl acetate
• CAS: 943222-40-0
• 化学式: C₁₄H₁₅ClN₄O₃
• 分子量: 322.751
• InChiKey: UODQMZGTCRTTLR-FTBFGRRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  82.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  acetic acid (1S,2R,4R,5R)-4-(6-chloro-9H-purin-9-yl)-1-methyl-6-oxa-bicyclo[3.1.0]hex-2-ylmethyl ester 在 氨 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以87%的产率得到((1S,2R,4R,5R)-4-(6-chloro-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：

  (1S,2S,4S,5R)-4-acetoxy-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 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 14.0h， 生成 acetic acid (1S,2R,4R,5R)-4-(6-chloro-9H-purin-9-yl)-1-methyl-6-oxa-bicyclo[3.1.0]hex-2-ylmethyl ester
  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