methyl 5-deoxy-α-D-xylofuranoside | 197011-66-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-deoxy-α-D-xylofuranoside
• 英文别名: (2S,3R,4R,5R)-2-methoxy-5-methyloxolane-3,4-diol
• CAS: 197011-66-8
• 化学式: C₆H₁₂O₄
• 分子量: 148.159
• InChiKey: UMFZEEAZPLDBDK-MOJAZDJTSA-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-α-D-xylofuranoside 在 吡啶 作用下， 以 吡啶 为溶剂， 反应 0.5h， 生成 methyl 2-O-acetyl-5-deoxy-3-O-(p-toluenesulfonyl)-α-D-xylofuranoside
  参考文献：
  名称：

  2,3-O-乙酰基-5-脱氧-α和β-D-木呋喃糖苷甲基的酶水解-猪肝酯酶的活性位点模型

  摘要：

  摘要甲基2,3-二-O-乙酰基-5-脱氧-α-D-木呋喃糖苷和2,3-二-O-乙酰基-5-脱氧-β-D-木呋喃糖苷的区域选择性酶水解（2）在存在猪肝酯酶（PLE）的条件下通过GLC进行了研究。双乙酸酯2仅生成3-O-乙酰基-5-脱氧-β-D-木呋喃糖苷甲基（6），而双乙酸酯1生成2-O-乙酰基-5-脱氧-α-D-木呋喃糖苷甲基（3）和甲基3 -O-乙酰基-5-脱氧-α-D-木呋喃糖苷（4）的收率低。在高转化率下，甲基5-脱氧-α-D-木呋喃糖苷（7）是唯一的产品。确定1、2和单乙酸3-6的一阶速率常数，Michaelis常数和最大速度。基于PLE的最新活性部位模型对结果进行解释。

  DOI：

  10.1080/07328309708005734
• 作为产物：
  描述：

  1,2-O-异亚丙基-alpha-D-呋喃木糖 在 镍 cation exchange resin (H form) 、 氢气 、 三乙胺 、 sodium iodide 作用下， 以 吡啶 、 甲醇 、 丁酮 为溶剂， 反应 14.0h， 生成 methyl 5-deoxy-α-D-xylofuranoside
  参考文献：
  名称：

  Methyl 5-Deoxy-α and β-D-Xylofuranosides

  摘要：

  Synthesized from D-xylose, methyl 5-deoxy-alpha-D-xylofuranoside (1) and methyl 5-deoxy-beta-D-xylofuranoside (2) were obtained in overall yields of 24 and 26 %, respectively. The key step in the synthesis was the separation of an anomeric mixture on a strong anion exchanger in OH- form. NMR data and mass spectra of title compounds 1, 2, methyl 2,3-di-O-acetyl-5-deoxy-alpha-D-xylofuranoside (3), and methyl 2,3-di-O-acetyl-5-deoxy-beta-D-xylofuranoside (4) are discussed. The conformations of 1 and 2 were established from the best fit between calculated and experimental coupling constants using Karplus equation.

  DOI：

  10.1080/07328309708005737

文献信息

• Kinetics of Methylation of Methyl 5-Deoxy-α/β-D-xylofuranosides
  作者：Mária Oščendová、Jitka Moravcová

  DOI：10.1135/cccc20041877

  日期：——

  The kinetics of methylation of methyl 5-deoxy-α-D-xylofuranoside (1), methyl 5-deoxy-β-D-xylofuranoside (2) and their partly methylated derivatives with methyl iodide in the presence of sodium hydroxide in acetonitrile was studied. The reaction rate was independent of the base concentration during the first half-time only and the methylation proceeded as a first-order reaction. The rate constants of all side and consecutive reactions were calculated and the influence of both polar and steric effect is discussed. The methylation of 1 was highly regioselective giving almost exclusively 5-deoxy-2-O-methyl-α-D-xylofuranoside.

  研究了在乙腈中，钠氢氧化物存在下，甲基碘对甲基5-去氧-α-D-木糖呋喃苷（1）、甲基5-去氧-β-D-木糖呋喃苷（2）及其部分甲基化衍生物的甲基化动力学。反应速率仅在前半个时间内与碱浓度无关，甲基化过程是一级反应。计算了所有副反应和连续反应的速率常数，并讨论了极性和立体效应的影响。1的甲基化高度选择性，几乎只产生5-去氧-2-O-甲基-α-D-木糖呋喃苷。
• Enzymic Hydrolysis of Methyl 2,3-<i>O</i>-Acetyl-5-Deoxy-α and β-D-Xylofuranosides - An Active-Site Model of Pig Liver Esterase
  作者：Jitka Moravcová、Zita Vanclová、Jindra Čapková、Karel Kefurt、Jan Staněk

  DOI：10.1080/07328309708005734

  日期：1997.9

  Abstract The regioselective enzymic hydrolysis of methyl 2,3-di-O-acetyl-5-deoxy-α-D-xylofuranoside (1) and methyl 2,3-di-O-acetyl-5-deoxy-β-D-xylofuranoside (2) in the presence of pig liver esterase (PLE) was studied by GLC. Diacetate 2 gave exclusively methyl 3-O-acetyl-5-deoxy-β-D-xylofuranoside (6) while diacetate 1 produced both methyl 2-O-acetyl-5-deoxy-α-D-xylofuranoside (3) and methyl 3-O-acetyl-5-deoxy-α-D-

  摘要甲基2,3-二-O-乙酰基-5-脱氧-α-D-木呋喃糖苷和2,3-二-O-乙酰基-5-脱氧-β-D-木呋喃糖苷的区域选择性酶水解（2）在存在猪肝酯酶（PLE）的条件下通过GLC进行了研究。双乙酸酯2仅生成3-O-乙酰基-5-脱氧-β-D-木呋喃糖苷甲基（6），而双乙酸酯1生成2-O-乙酰基-5-脱氧-α-D-木呋喃糖苷甲基（3）和甲基3 -O-乙酰基-5-脱氧-α-D-木呋喃糖苷（4）的收率低。在高转化率下，甲基5-脱氧-α-D-木呋喃糖苷（7）是唯一的产品。确定1、2和单乙酸3-6的一阶速率常数，Michaelis常数和最大速度。基于PLE的最新活性部位模型对结果进行解释。
• Methyl 5-Deoxy-α and β-D-Xylofuranosides
  作者：Jitka Moravcová、Jindra Čapková、Jan Staněk、Ivan Raich

  DOI：10.1080/07328309708005737

  日期：1997.9

  Synthesized from D-xylose, methyl 5-deoxy-alpha-D-xylofuranoside (1) and methyl 5-deoxy-beta-D-xylofuranoside (2) were obtained in overall yields of 24 and 26 %, respectively. The key step in the synthesis was the separation of an anomeric mixture on a strong anion exchanger in OH- form. NMR data and mass spectra of title compounds 1, 2, methyl 2,3-di-O-acetyl-5-deoxy-alpha-D-xylofuranoside (3), and methyl 2,3-di-O-acetyl-5-deoxy-beta-D-xylofuranoside (4) are discussed. The conformations of 1 and 2 were established from the best fit between calculated and experimental coupling constants using Karplus equation.