1-phenyl-2,3,4,6-tetra-O-acetyl-β-D-allopyranoside | 887229-12-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-phenyl-2,3,4,6-tetra-O-acetyl-β-D-allopyranoside
• 英文别名: [(2R,3R,4R,5R,6S)-3,4,5-triacetyloxy-6-phenoxyoxan-2-yl]methyl acetate
• CAS: 887229-12-1
• 化学式: C₂₀H₂₄O₁₀
• 分子量: 424.405
• InChiKey: HPKPFIHCMIKXMU-LASHMREHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.15
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1-phenyl-2,3,4,6-tetra-O-acetyl-β-D-allopyranoside 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 120.0h， 以95%的产率得到1,6-anhydro-β-D-allopyranose
  参考文献：
  名称：

  On the Regioselective Acylation of 1,6-Anhydro-β-d- andl-Hexopyranoses Catalysed by Lipases: Structural Basis and Synthetic Applications

  摘要：

  With the aim of providing new methods for the regioselective protection at the 2, 3 and 4 positions of monosaccharides, we have studied the acetylation of a class of rigid sugars: the 1,6-anhydro-beta-D- and L-hexopyranoses (hexopyranosanes D-l to D-5 and L-1 to L-5), using vinyl acetate as an acyl donor and two common lipases,Candida rugosa and Pseudomonas cepacia, as catalysts. Our results indicate that the relative orientation of the hydroxyls governs the regioselectivity of acetylation. In the D-series, when the 3-OH is in the axial position, acetylation occurs mainly at the 4-axial OH, while the 2-axial OH is preferred when the 4-OH is equatorial. Conversely, when the 3-OH is equatorial, a strong selectivity affects the equatorial 2-OH. Compounds of the L-series were shown to be poor substrates for the lipase Pseudomonas cepacia except for L-galactosane for which the 2-monoacetyl ester was obtained in good yield. An attempt to rationalize the results by means of molecular modelling is also made to account for the catalytic activity of the Candida rugosa lipase on hexopyranosanes 1-3.

  DOI：

  10.1080/07328309808005771
• 作为产物：
  描述：

  苯酚 、 pentaacetyl β-D-allose 在 对甲苯磺酸 作用下， 90.0 ℃ 、2.0 kPa 条件下， 反应 1.5h， 生成 1-phenyl-2,3,4,6-tetra-O-acetyl-β-D-allopyranoside
  参考文献：
  名称：

  On the Regioselective Acylation of 1,6-Anhydro-β-d- andl-Hexopyranoses Catalysed by Lipases: Structural Basis and Synthetic Applications

  摘要：

  With the aim of providing new methods for the regioselective protection at the 2, 3 and 4 positions of monosaccharides, we have studied the acetylation of a class of rigid sugars: the 1,6-anhydro-beta-D- and L-hexopyranoses (hexopyranosanes D-l to D-5 and L-1 to L-5), using vinyl acetate as an acyl donor and two common lipases,Candida rugosa and Pseudomonas cepacia, as catalysts. Our results indicate that the relative orientation of the hydroxyls governs the regioselectivity of acetylation. In the D-series, when the 3-OH is in the axial position, acetylation occurs mainly at the 4-axial OH, while the 2-axial OH is preferred when the 4-OH is equatorial. Conversely, when the 3-OH is equatorial, a strong selectivity affects the equatorial 2-OH. Compounds of the L-series were shown to be poor substrates for the lipase Pseudomonas cepacia except for L-galactosane for which the 2-monoacetyl ester was obtained in good yield. An attempt to rationalize the results by means of molecular modelling is also made to account for the catalytic activity of the Candida rugosa lipase on hexopyranosanes 1-3.

  DOI：

  10.1080/07328309808005771