Octyl 2,4-di-O-acetyl-β-D-xylopyranoside | 159501-59-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Octyl 2,4-di-O-acetyl-β-D-xylopyranoside
• 英文别名: [(3R,4S,5R,6R)-5-acetyloxy-4-hydroxy-6-octoxyoxan-3-yl] acetate
• CAS: 159501-59-4
• 化学式: C₁₇H₃₀O₇
• 分子量: 346.421
• InChiKey: XTIANSVDGVUMTR-YYIAUSFCSA-N

物化性质

• 沸点：
  449.5±45.0 °C(predicted)
• 密度：
  1.12±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Octyl 2,4-di-O-acetyl-β-D-xylopyranoside 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 Octyl 3-O-(β-D-galactopyranosyl)-β-D-xylopyranoside
  参考文献：
  名称：

  Regioselective Acetylations of Alkyl .beta.-D-Xylopyranosides by Use of Lipase PS in Organic Solvents and Application to the Chemoenzymic Synthesis of Oligosaccharides

  摘要：

  Aglycon structure and solvent can change the regioselectivity of the acetylation of alkyl beta-D-xylopyranosides, catalyzed by lipase PS. The acetylation of methyl beta-D-xylopyranoside (3) in acetonitrile gave the 3,4-diacetate 4 exclusively, whereas the reaction of octyl beta-D-xylopyranoside (5) gave a mixture of 2,4- and 3,4-diacetates (6 and 7) in 1.0:1.3 and 3.6:1.0 ratios, in acetonitrile and hexane, respectively. The effect of several solvents on the selectivity in the monoacetylation of 5 was studied. The 2-monoacetate 8 was preferentially formed over the 3- and 4-monoacetates (9 and 10) in hydrophobic solvents. High yields of partially acetylated xylose derivatives were obtained, which were used in the syntheses of a disaccharide showing liquid crystal properties, an intermediate for the synthesis of proteoglycan fragments, and a trisaccharide potential inhibitor of plant growth.

  DOI：

  10.1021/jo00102a029
• 作为产物：
  描述：

  乙酸乙烯酯 、 1-octyl-β-D-xylopyranoside 在 4 A molecular sieve 作用下， 以 正己烷 为溶剂， 反应 74.0h， 以70%的产率得到Octyl 2,4-di-O-acetyl-β-D-xylopyranoside
  参考文献：
  名称：

  Regioselective Acetylations of Alkyl .beta.-D-Xylopyranosides by Use of Lipase PS in Organic Solvents and Application to the Chemoenzymic Synthesis of Oligosaccharides

  摘要：

  Aglycon structure and solvent can change the regioselectivity of the acetylation of alkyl beta-D-xylopyranosides, catalyzed by lipase PS. The acetylation of methyl beta-D-xylopyranoside (3) in acetonitrile gave the 3,4-diacetate 4 exclusively, whereas the reaction of octyl beta-D-xylopyranoside (5) gave a mixture of 2,4- and 3,4-diacetates (6 and 7) in 1.0:1.3 and 3.6:1.0 ratios, in acetonitrile and hexane, respectively. The effect of several solvents on the selectivity in the monoacetylation of 5 was studied. The 2-monoacetate 8 was preferentially formed over the 3- and 4-monoacetates (9 and 10) in hydrophobic solvents. High yields of partially acetylated xylose derivatives were obtained, which were used in the syntheses of a disaccharide showing liquid crystal properties, an intermediate for the synthesis of proteoglycan fragments, and a trisaccharide potential inhibitor of plant growth.

  DOI：

  10.1021/jo00102a029