Methyl-5-deoxy-β-D-arabinofuranosid | 216660-03-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl-5-deoxy-β-D-arabinofuranosid
• 英文别名: (2R,3S,4S,5R)-2-methoxy-5-methyloxolane-3,4-diol
• CAS: 216660-03-6
• 化学式: C₆H₁₂O₄
• 分子量: 148.159
• InChiKey: UMFZEEAZPLDBDK-ARQDHWQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl-5-deoxy-β-D-arabinofuranosid 、 乙酸酐 以 吡啶 为溶剂， 反应 1.0h， 以28%的产率得到methyl 3-O-acetyl-5-deoxy-β-D-arabinofuranoside
  参考文献：
  名称：

  Pig Liver Esterase Catalyzed Hydrolysis of Methyl 2,3-Di-O-Acetyl-5-Deoxy-α- and β-D-Arabinofuranosides

  摘要：

  The regioselectivity of a pig liver esterase (PLE) catalyzed hydrolysis of methyl 2,3-di-O-acetyl-5-deoxy-alpha-D-arabinofuranoside (1) and methyl 2,3-di-O-acetyl-5-deoxy-beta-D-arabinofuranoside (2) was established by GLC. Diacetate 1 gave exclusively methyl 3-O-acetyl-5-deoxy-alpha-D-arabinofuranoside while diacetate 2 produced both methyl 2-O-acetyl-5-deoxy-beta-D-arabinofuranoside and methyl 3-O-acetyl-5-deoxy-beta-D-arabinofuranoside which were resistant to subsequent hydrolysis. The Michaelis constants and maximal velocities were determined for 1 and 2. The first-order rate constants were computed for 1, 2, and all corresponding monoacetates. The results were evaluated on the basis of a Jones's active-site model for PLE and the additional criteria valid for acetyl esters of pentofuranosides were proposed.

  DOI：

  10.1080/07328309808001893
• 作为产物：
  描述：

  methyl 2-O-acetyl-5-deoxy-β-D-arabinofuranoside 在 pig liver esterase sodium hydroxide 作用下， 以 various solvent(s) 为溶剂， 生成 Methyl-5-deoxy-β-D-arabinofuranosid
  参考文献：
  名称：

  Pig Liver Esterase Catalyzed Hydrolysis of Methyl 2,3-Di-O-Acetyl-5-Deoxy-α- and β-D-Arabinofuranosides

  摘要：

  The regioselectivity of a pig liver esterase (PLE) catalyzed hydrolysis of methyl 2,3-di-O-acetyl-5-deoxy-alpha-D-arabinofuranoside (1) and methyl 2,3-di-O-acetyl-5-deoxy-beta-D-arabinofuranoside (2) was established by GLC. Diacetate 1 gave exclusively methyl 3-O-acetyl-5-deoxy-alpha-D-arabinofuranoside while diacetate 2 produced both methyl 2-O-acetyl-5-deoxy-beta-D-arabinofuranoside and methyl 3-O-acetyl-5-deoxy-beta-D-arabinofuranoside which were resistant to subsequent hydrolysis. The Michaelis constants and maximal velocities were determined for 1 and 2. The first-order rate constants were computed for 1, 2, and all corresponding monoacetates. The results were evaluated on the basis of a Jones's active-site model for PLE and the additional criteria valid for acetyl esters of pentofuranosides were proposed.

  DOI：

  10.1080/07328309808001893