5-O-butyryl-D-ribofuranose | 146572-28-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-O-butyryl-D-ribofuranose
• 英文别名: [(2R,3S,4R)-3,4,5-trihydroxyoxolan-2-yl]methyl butanoate
• CAS: 146572-28-3；146572-29-4；146572-34-1；146572-35-2
• 化学式: C₉H₁₆O₆
• 分子量: 220.222
• InChiKey: YLCFYORYWZQSNA-HDPJAJKNSA-N

物化性质

• 沸点：
  373.3±42.0 °C(predicted)
• 密度：
  1.365±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  丁酸酐 、 5-O-butyryl-D-ribofuranose 在 吡啶 作用下， 生成 1,2,3,5-tetra-O-butanoyl-D-ribofuranoside
  参考文献：
  名称：

  Effect of acyl chain length on selective biocatalytic deacylation on O-aryl glycosides and separation of anomers

  摘要：

  It has been demonstrated that Lipozyme (R) TL IM (Thermomyces lanuginosus lipase immobilised on silica) can selectively deacylate the ester function involving the C-5' hydroxyl group of alpha-anomers over the other acyl functions of anomeric mixture of peracylated O-aryl alpha,beta-D-ribofuranoside. The analysis of results of biocatalytic deacylation reaction revealed that the reaction time decreases with the increase in the acyl chain length from C-1 to C-4. The unique selectivity of Lipozyme (R) TL IM has been harnessed for the separation of anomeric mixture of peracylated O-aryl alpha,beta-D-ribofuranosides, The lipase mediated selective deacylation methodology has been used for the synthesis of O-aryl alpha-D-ribofuranosides and O-aryl beta-D-ribofuranosides in pure forms, which can be used as chromogenic substrate for the detection of pathogenic microbial parasites containing glycosidases. (C) 2014 Published by Elsevier Inc.

  DOI：

  10.1016/j.bioorg.2014.02.004
• 作为产物：
  描述：

  丁酸酐 、 D-核糖 在 Candida antarctica lipase B 作用下， 以 四氢呋喃 为溶剂， 生成 5-O-butyryl-D-ribofuranose
  参考文献：
  名称：

  Effect of acyl chain length on selective biocatalytic deacylation on O-aryl glycosides and separation of anomers

  摘要：

  It has been demonstrated that Lipozyme (R) TL IM (Thermomyces lanuginosus lipase immobilised on silica) can selectively deacylate the ester function involving the C-5' hydroxyl group of alpha-anomers over the other acyl functions of anomeric mixture of peracylated O-aryl alpha,beta-D-ribofuranoside. The analysis of results of biocatalytic deacylation reaction revealed that the reaction time decreases with the increase in the acyl chain length from C-1 to C-4. The unique selectivity of Lipozyme (R) TL IM has been harnessed for the separation of anomeric mixture of peracylated O-aryl alpha,beta-D-ribofuranosides, The lipase mediated selective deacylation methodology has been used for the synthesis of O-aryl alpha-D-ribofuranosides and O-aryl beta-D-ribofuranosides in pure forms, which can be used as chromogenic substrate for the detection of pathogenic microbial parasites containing glycosidases. (C) 2014 Published by Elsevier Inc.

  DOI：

  10.1016/j.bioorg.2014.02.004

文献信息

• Pulido, Rosalino; Ortiz, Fernando Lopez; Gotor, Vicente, Journal of the Chemical Society. Perkin transactions I, 1992, # 21, p. 2891 - 2898
  作者：Pulido, Rosalino、Ortiz, Fernando Lopez、Gotor, Vicente

  DOI：——

  日期：——
• Sharma, Raman K.; Aggarwal, Neha; Arya, Anu, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2009, vol. 48, # 12, p. 1727 - 1731
  作者：Sharma, Raman K.、Aggarwal, Neha、Arya, Anu、Olsen, Carl E.、Parmar, Virinder S.、Prasad, Ashok K.

  DOI：——

  日期：——
• Diastereoselective and regioselective reactions on D-aldopentose mixtures: A possible reason for nature's choice of D-ribofuranose based nucleic acids?
  作者：Jesper Wengel、Claus Scheuer-Larsen

  DOI：10.1016/s0960-894x(97)00352-1

  日期：1997.8

  Remarkably diastereoselective and regioselective reactions on an equimolar mixture of D-ribose, D-arabinose, D-xylose and D-lyxose are reported to give 5-O-functionalised D-ribofuranose derivatives. (C) 1997 Elsevier Science Ltd.
• Effect of acyl chain length on selective biocatalytic deacylation on O-aryl glycosides and separation of anomers
  作者：Neha Aggarwal、Anu Arya、Divya Mathur、Sukhdev Singh、Abhilash Tyagi、Rajesh Kumar、Neha Rana、Rajendra Singh、Ashok K. Prasad

  DOI：10.1016/j.bioorg.2014.02.004

  日期：2014.4

  It has been demonstrated that Lipozyme (R) TL IM (Thermomyces lanuginosus lipase immobilised on silica) can selectively deacylate the ester function involving the C-5' hydroxyl group of alpha-anomers over the other acyl functions of anomeric mixture of peracylated O-aryl alpha,beta-D-ribofuranoside. The analysis of results of biocatalytic deacylation reaction revealed that the reaction time decreases with the increase in the acyl chain length from C-1 to C-4. The unique selectivity of Lipozyme (R) TL IM has been harnessed for the separation of anomeric mixture of peracylated O-aryl alpha,beta-D-ribofuranosides, The lipase mediated selective deacylation methodology has been used for the synthesis of O-aryl alpha-D-ribofuranosides and O-aryl beta-D-ribofuranosides in pure forms, which can be used as chromogenic substrate for the detection of pathogenic microbial parasites containing glycosidases. (C) 2014 Published by Elsevier Inc.