1,6-anhydro-3,4-di-O-acetyl-β-D-glucopyranose | 23740-50-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 1,6-anhydro-3,4-di-O-acetyl-β-D-glucopyranose
• 英文别名: [(1R,2R,3R,4R,5R)-3-acetyloxy-4-hydroxy-6,8-dioxabicyclo[3.2.1]octan-2-yl] acetate
• CAS: 23740-50-3
• 化学式: C₁₀H₁₄O₇
• 分子量: 246.217
• InChiKey: BHHLZFFKLMKOBD-VVULQXIFSA-N

物化性质

• 沸点：
  355.0±42.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  三甲基氯硅烷 、 1,6-anhydro-3,4-di-O-acetyl-β-D-glucopyranose 以 吡啶 、 formamide 为溶剂， 生成 Acetic acid (1R,2R,3S,4R,5R)-2-acetoxy-4-trimethylsilanyloxy-6,8-dioxa-bicyclo[3.2.1]oct-3-yl ester
  参考文献：
  名称：

  Schraml, Jan; Kucar, Stefan; Zeleny, Jan, Collection of Czechoslovak Chemical Communications, 1985, vol. 50, # 5, p. 1176 - 1183

  摘要：

  DOI：
• 作为产物：
  描述：

  1,6-脱水-β-D-葡萄糖-2,3,4-三邻醋酸 生成 1,6-anhydro-3,4-di-O-acetyl-β-D-glucopyranose
  参考文献：
  名称：

  ZEMEK, JIRI;KUCAR, STEFAN;ZAMOCKY, JURAJ

  摘要：

  DOI：

文献信息

• Regioselective acylation of 1,6-anhydro-β-D-glucopyranose catalysed by lipases
  作者：C. Chon、A. Heisler、N. Junot、F. Levayer、C. Rabiller

  DOI：10.1016/s0957-4166(00)82220-x

  日期：1993.1

  Pseudomonas fluorescens lipase (Amano) was found to be highly regioselective (85%) in the catalysed transesterification of 1,6-anhydro-β-D-glucopyranose using vinyl acetate as an acyl donor and solvent.

  在以乙酸乙烯酯为酰基供体和溶剂的1,6-脱水-β-D-吡喃葡萄糖催化的酯交换反应中，荧光假单胞菌脂肪酶（Amano）具有很高的区域选择性（85％）。
• On the Regioselective Acylation of 1,6-Anhydro-β-<scp>d</scp>- and<scp>l</scp>-Hexopyranoses Catalysed by Lipases: Structural Basis and Synthetic Applications
  作者：Nathalie Boissièere-Junot、Charles Tellier、Claude Rabiller

  DOI：10.1080/07328309808005771

  日期：1998.1

  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.
• Zemek, Jiri; Kucar, Stefan; Anderle, Dusan, Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 9, p. 2347 - 2352
  作者：Zemek, Jiri、Kucar, Stefan、Anderle, Dusan

  DOI：——

  日期：——
• Kucar, Stefan; Zamocky, Juraj; Zemek, Juraj, Collection of Czechoslovak Chemical Communications, 1984, vol. 49, # 8, p. 1780 - 1787
  作者：Kucar, Stefan、Zamocky, Juraj、Zemek, Juraj、Anderle, Dusan、Matulova, Maria

  DOI：——

  日期：——
• Regioselective acylation of 1,6-anhydro-β-D-manno and galactopyranose catalysed by lipases
  作者：N. Junot、J.C. Meslin、C. Rabiller

  DOI：10.1016/0957-4166(95)00171-k

  日期：1995.6

  Pseudomonas fluorescens lipase (Amano) was found to be highly regioselective in the transesterification of 1,6-anhydro-beta-D-manno and galactopyranoses (mannosane curd galactosane respectively) using vinyl acetate as an acyl donor. As in the case of 1,6-anhydro-beta-D-glucopyranose (glucosane), the 4-OH axial group of mannosane is preferred, while the titled lipase catalysed the regioselective transesterification at the 2-axial OH of galactosane. The enzymatic acylation affords monoesters of the 1,6-anhydropyranoses which are difficult to obtain using conventional methods.