5-deoxy-L-arabinose | 93978-94-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-deoxy-L-arabinose
• 英文别名: (3R,4R,5S)-5-methyloxolane-2,3,4-triol
• CAS: 93978-94-0；93978-95-1；113421-68-4；113421-69-5；113421-70-8；113421-71-9；113421-72-0；113421-73-1
• 化学式: C₅H₁₀O₄
• 分子量: 134.132
• InChiKey: MKMRBXQLEMYZOY-HWQSCIPKSA-N

物化性质

• 沸点：
  277.7±40.0 °C(Predicted)
• 密度：
  1.478±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-deoxy-L-arabinose 在 吡啶 、 sodium tetrahydroborate 作用下， 反应 5.0h， 生成 L-Arabinitol, 5-deoxy-, tetraacetate
  参考文献：
  名称：

  Acyclic stereoselection. 32. Synthesis and characterization of the diastereomeric (4S)-pentane-1,2,3,4-tetraols

  摘要：

  DOI：

  10.1021/jo00218a001
• 作为产物：
  描述：

  5-脱氧-L-阿拉伯糖酸GAMMA-内酯 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.5h， 生成 5-deoxy-L-arabinose
  参考文献：
  名称：

  Highly α-Selective Hydrolysis of α,β-Epoxyalcohols using Tetrabutylammonium Fluoride

  摘要：

  We report a simple method for the highly regio- and stereoselective hydrolysis of alpha,beta-epoxyalcohols. Treatment of enantiopure epoxyalcohols derived from Sharpless epoxidation with TBAF/H(2)O resulted in exclusive ring opening at the normally disfavored alpha-position, providing access to arabino- or lyxo-configured triols with full preservation of stereochemical purity. The method was applied in syntheses of 5-deoxy-L-arabinose (26) and a family of bicyclic acetals based on the insect pheromone hydroxybrevicomin (4).

  DOI：

  10.1021/ol1015306

文献信息

• Total Synthesis of <scp>l</scp>-Biopterin from <scp>l</scp>-Tartaric Acid <i>via</i> 5-Deoxy-<scp>l</scp>-arabinose
  作者：Anne-Marie Fernandez、Lucette Duhamel

  DOI：10.1021/jo961426s

  日期：1996.1.1
• The influence of microwave irradiation on stereospecific Mo(VI)-catalyzed transformation of deoxysugars
  作者：Zuzana Hricovíniová

  DOI：10.1016/j.tetasy.2009.05.010

  日期：2009.6

  The stereospecific mutual isomerization of 5-, 6-, and 7-deoxysugars in a microwave field with Mo(VI) as a catalyst is reported. The reaction cycle allows the use of catalytic amounts of molybdate ions to form highly reactive catalytically active dimolybdate complexes that create conditions for stereospecific intramolecular rearrangement. The microwave-enhanced Mo(VI)-catalyzed transformation of deoxyaldoses occurred with full stereospecificity resulting in the formation of the corresponding epi-deoxyaldoses in very good yields. The microwave field has a Substantial effect on the transformation studied. (C) 2009 Elsevier Ltd. All rights reserved.
• Acyclic stereoselection. 32. Synthesis and characterization of the diastereomeric (4S)-pentane-1,2,3,4-tetraols
  作者：Kazuhiko Takai、Clayton H. Heathcock

  DOI：10.1021/jo00218a001

  日期：1985.9
• Highly α-Selective Hydrolysis of α,β-Epoxyalcohols using Tetrabutylammonium Fluoride
  作者：Purba Mukerjee、Mohammed Abid、Frank C. Schroeder

  DOI：10.1021/ol1015306

  日期：2010.9.17

  We report a simple method for the highly regio- and stereoselective hydrolysis of alpha,beta-epoxyalcohols. Treatment of enantiopure epoxyalcohols derived from Sharpless epoxidation with TBAF/H(2)O resulted in exclusive ring opening at the normally disfavored alpha-position, providing access to arabino- or lyxo-configured triols with full preservation of stereochemical purity. The method was applied in syntheses of 5-deoxy-L-arabinose (26) and a family of bicyclic acetals based on the insect pheromone hydroxybrevicomin (4).