acetic acid (1S,3R,5S)-3-hydroxy-5-methyl-6-oxabicyclo[3.1.0]hex-1-ylmethyl ester | 1007861-03-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: acetic acid (1S,3R,5S)-3-hydroxy-5-methyl-6-oxabicyclo[3.1.0]hex-1-ylmethyl ester
• 英文别名: [(1S,3R,5S)-3-hydroxy-5-methyl-6-oxabicyclo[3.1.0]hexan-1-yl]methyl acetate
• CAS: 1007861-03-1
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: HXEABWWFIVYXJG-VGMNWLOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.23
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  59.06
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  acetic acid (1S,3R,5S)-3-hydroxy-5-methyl-6-oxabicyclo[3.1.0]hex-1-ylmethyl ester 、 2-氨基-6-氯嘌呤 在 偶氮二甲酸二异丙酯 、 三苯基膦 、 氨 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 22.5h， 以70%的产率得到[(1S,3S,5S)-3-(2-amino-6-chloropurin-9-yl)-5-methyl-6-oxabicyclo[3.1.0]hex-1-yl]methanol
  参考文献：
  名称：

  Chemoenzymatic synthesis and antiviral evaluation of conformationally constrained and 3′-methyl-branched carbanucleosides using both enantiomers of the same building block

  摘要：

  Starting from both enantiomers of a readily available building block, a straightforward enantioselective approach to constrained 3'-methyl-2',3'-alpha-oxirane-fused and 3'-methyl-3',4'-alpha-oxirane-fused carbanucleosides bearing different purine base analogues is described. The title compounds were evaluated as potential antiviral agents against important viruses. None of the new compounds had significant antiviral activity at a concentration of 100 mu g/mL, which was the highest concentration tested. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.09.030
• 作为产物：
  描述：

  acetic acid (R)-4-hydroxy-2-methylcyclopent-1-enylmethyl ester 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 水 为溶剂， 以91%的产率得到acetic acid (1S,3R,5S)-3-hydroxy-5-methyl-6-oxabicyclo[3.1.0]hex-1-ylmethyl ester
  参考文献：
  名称：

  Chemoenzymatic synthesis and antiviral evaluation of conformationally constrained and 3′-methyl-branched carbanucleosides using both enantiomers of the same building block

  摘要：

  Starting from both enantiomers of a readily available building block, a straightforward enantioselective approach to constrained 3'-methyl-2',3'-alpha-oxirane-fused and 3'-methyl-3',4'-alpha-oxirane-fused carbanucleosides bearing different purine base analogues is described. The title compounds were evaluated as potential antiviral agents against important viruses. None of the new compounds had significant antiviral activity at a concentration of 100 mu g/mL, which was the highest concentration tested. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.09.030