1-(6-allyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethane-1,2-diol | 932020-00-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(6-allyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethane-1,2-diol
• CAS: 932020-00-3
• 化学式: C₁₂H₂₀O₅
• 分子量: 244.288
• InChiKey: ISWZJOKVUYIUKG-OGBGREFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.41
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  68.15
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-(6-allyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethane-1,2-diol 在 palladium on activated charcoal sodium tetrahydroborate 、 sodium periodate 、 乙醇 、 硫酸 、 对甲苯磺酸 、 三乙胺 、 环己烯 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 、 正丁醇 为溶剂， 反应 89.0h， 生成 (1S,2S,3S,5R)-2-(6-chloropurin-9-yl)-3,5-bis(hydroxymethyl)cyclopentan-1-ol
  参考文献：
  名称：

  Carbanucleosides: synthesis of both enantiomers of 2-(6-chloro-purin-9-yl)-3,5-bishydroxymethyl cyclopentanol from d-glucose

  摘要：

  The key intermediate 1,2:5,6-di-O-isopropylidene-3-deoxy-3 beta-allyl-alpha-D-glucofuranose (8) could be conveniently prepared through radical induced allyl substitution at C-3 of appropriate 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose derivatives (7a,b) and used to synthesize enantiomeric bishydroxymethyl aminocyclopentanols 13 and 19 by the application of a 1,3-dipolar nitrone cycloaddition reaction involving the C-5 or C-1 aldehyde functionality. The products were subsequently transformed into carbanucleoside enantiomers 15 and 21. The diastercomeric isoxazolidinocyclopentane derivative 20 was similarly converted to carbanucleoside 22. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.10.070
• 作为产物：
  描述：

  1,2,5,6-di-O-isopropylidene-α-D-glucofuranose-3-O-(S-methylxanthate) 在 偶氮二异丁腈 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 0.5h， 生成 1-(6-allyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethane-1,2-diol
  参考文献：
  名称：

  Carbanucleosides: synthesis of both enantiomers of 2-(6-chloro-purin-9-yl)-3,5-bishydroxymethyl cyclopentanol from d-glucose

  摘要：

  The key intermediate 1,2:5,6-di-O-isopropylidene-3-deoxy-3 beta-allyl-alpha-D-glucofuranose (8) could be conveniently prepared through radical induced allyl substitution at C-3 of appropriate 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose derivatives (7a,b) and used to synthesize enantiomeric bishydroxymethyl aminocyclopentanols 13 and 19 by the application of a 1,3-dipolar nitrone cycloaddition reaction involving the C-5 or C-1 aldehyde functionality. The products were subsequently transformed into carbanucleoside enantiomers 15 and 21. The diastercomeric isoxazolidinocyclopentane derivative 20 was similarly converted to carbanucleoside 22. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.10.070