1,2:5,6-di-O-isopropylidene-3-deoxy-3β-allyl-α-D-glucofuranose | 173910-65-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2:5,6-di-O-isopropylidene-3-deoxy-3β-allyl-α-D-glucofuranose
• 英文别名: 3-C-allyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose；(3aR,5S,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6-prop-2-enyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 173910-65-1
• 化学式: C₁₅H₂₄O₅
• 分子量: 284.353
• InChiKey: YNVHQHRHCGJRIV-OBPIAQAESA-N

物化性质

• 沸点：
  330.9±42.0 °C(Predicted)
• 密度：
  1.066±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,2:5,6-di-O-isopropylidene-3-deoxy-3β-allyl-α-D-glucofuranose 在 Grubbs catalyst first generation sodium hydroxide 、 四(三苯基膦)钯 、 硫酸 、 sodium hydride 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 乙腈 为溶剂， 反应 79.75h， 生成 (-)-卡巴韦
  参考文献：
  名称：

  A short and efficient synthesis of 5-hydroxymethylcyclopent-2-enol from d-glucose and its elaboration to the carbanucleoside (−)-carbovir

  摘要：

  Introduction of an allyl functionality at C-3 of 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose followed by olefination at C-5 and C-6 provided 1,6-diene 5 which, upon ring closing metathesis and subsequent functional group manipulation, furnished the key cyclopentene diacetate 7, which was elaborated to carbanucleoside (-)-carbovir 1. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.01.016
• 作为产物：
  描述：

  烯丙基三丁基锡 、 1,2,5,6-di-O-isopropylidene-α-D-glucofuranose-3-O-(S-methylxanthate) 在 偶氮二异丁腈 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以35%的产率得到1,2:5,6-di-O-isopropylidene-3-deoxy-3β-allyl-α-D-glucofuranose
  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

文献信息

• Carbanucleosides: synthesis of both enantiomers of 2-(6-chloro-purin-9-yl)-3,5-bishydroxymethyl cyclopentanol from d-glucose
  作者：Biswajit G. Roy、Joy Krishna Maity、Michael G.B. Drew、Basudeb Achari、Sukhendu B. Mandal

  DOI：10.1016/j.tetlet.2006.10.070

  日期：2006.12

  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.
• A short and efficient synthesis of 5-hydroxymethylcyclopent-2-enol from d-glucose and its elaboration to the carbanucleoside (−)-carbovir
  作者：Biswajit G. Roy、Prithwish K. Jana、Basudeb Achari、Sukhendu B. Mandal

  DOI：10.1016/j.tetlet.2007.01.016

  日期：2007.2

  Introduction of an allyl functionality at C-3 of 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose followed by olefination at C-5 and C-6 provided 1,6-diene 5 which, upon ring closing metathesis and subsequent functional group manipulation, furnished the key cyclopentene diacetate 7, which was elaborated to carbanucleoside (-)-carbovir 1. (c) 2007 Elsevier Ltd. All rights reserved.