3,5-di-O-acetyl-α-D-2-deoxyarabinofuranoside | 23701-40-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,5-di-O-acetyl-α-D-2-deoxyarabinofuranoside
• 英文别名: methyl 3,5-di-O-acetyl-2-deoxy-α-D-ribofuranoside；methyl 3,5-di-O-acetyl-2-deoxy-α-D-ribofuranose；[(2R,3S,5S)-3-acetyloxy-5-methoxyoxolan-2-yl]methyl acetate
• CAS: 23701-40-8
• 化学式: C₁₀H₁₆O₆
• 分子量: 232.233
• InChiKey: MBNZXGFEXJLTGC-AEJSXWLSSA-N

物化性质

• 沸点：
  295.9±40.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,5-di-O-acetyl-α-D-2-deoxyarabinofuranoside 生成 methyl 5-O-acetyl-2-deoxy-α-D-ribofuranoside
  参考文献：
  名称：

  HENNEN, WILLIAM J.;SWEERS, H. MARCEL;WANG, YI-FONG;WONG, CHI-HUEY, J. ORG. CHEM., 53,(1988) N 21, C. 4939-4945

  摘要：

  DOI：
• 作为产物：
  描述：

  [(2R,3R,4S,5S)-3-acetyloxy-4-(imidazole-1-carbothioyloxy)-5-methoxyoxolan-2-yl]methyl acetate 在 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 、 亚膦酸 、 三乙胺 作用下， 以 乙二醇二甲醚 为溶剂， 反应 2.0h， 以60%的产率得到3,5-di-O-acetyl-α-D-2-deoxyarabinofuranoside
  参考文献：
  名称：

  Selective monodeacetylation of methyl 2,3,5-tri-O-acetyl-d-arabinofuranoside using biocatalyst

  摘要：

  Methyl arabinofuranoside 1 was fully acetylated to methyl 2,3,5-tri-O-acetyl-D-arabinofuranoside 2 and it was regio-selectively deacetylated using enzymes. Rhizopus oryzae esterase gave methyl 3,5-di-O-acetyl-D-arabinofuranoside 3, regioselectively. This protected 3 was deoxygenized to 3,5-di-O-acetyl-D-2-deoxyarabinofuranoside 7 using hypophosphorous acid. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.120

文献信息

• Enzymes in carbohydrate synthesis. Lipase-catalyzed selective acylation and deacylation of furanose and pyranose derivatives
  作者：William J. Hennen、H. Marcel Sweers、Yi Fong Wang、Chi Huey Wong

  DOI：10.1021/jo00256a008

  日期：1988.10
• New stable anomeric hydroperoxides derived from 2-deoxysugars; enantioselective epoxidation of 2-methyl-1,4-naphthoquinone
  作者：Wioletta Kośnik、Andrew V. Stachulski、Marek Chmielewski

  DOI：10.1016/j.tetasy.2005.04.009

  日期：2005.6

  3.5-Di- or 3,4,6-tri-O-substituted-2-deoxysugars or their glycosides can be oxidized with hydrogen peroxide in the presence of an acid catalyst to the corresponding anomeric hydroperoxides, which are relatively stable, can be separated into pure anomers by column chromatography and stored in a refrigerator without visible decomposition. The hydroperoxides thus obtained were used for the enantioselective epoxidation of 2-methyl-1,4-naphthoquinone with ees in the range 28-47%. (c) 2005 Elsevier Ltd. All rights reserved.
• Diastereoselective enzymatic preparation of acetylated pentofuranosides carrying free 5-hydroxyl groups
  作者：Esteban D. Gudiño、Adolfo M. Iribarren、Luis E. Iglesias

  DOI：10.1016/j.tetasy.2009.07.001

  日期：2009.8

  Methyl 3-O-acetyl-2-deoxy-alpha-D-ribofuranoside, 1,3-di-O-acetyl-2-deoxy-alpha-D-ribofuranose and 1,2,3-tri-O-acetyl-alpha-D-arabinofuranose were diastereoselectively prepared (de = 100%) from anomeric mixtures of the corresponding 5-acetylated compounds through Candida antarctica B lipase (CAL B)-catalysed alcoholysis. (c) 2009 Elsevier Ltd. All rights reserved.