2-O-acetyl-1,3,4,5-tetra-O-benzoyl-β-D-fructopyranose | 155137-98-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-O-acetyl-1,3,4,5-tetra-O-benzoyl-β-D-fructopyranose
• 英文别名: 1,3,4,5-tetra-O-benzoyl-β-D-fructopyranosyl-2-O-acetate；1,3,4,5-tetra-O-benzoyl-D-fructopyranosyl acetate；2-Acetyl-1,3,4,5-tetrabenzoyl-β-D-fructopyranose；O²-Acetyl-O¹,O³,O⁴,O⁵-tetrabenzoyl-β-D-fructopyranose；[(2S,3S,4R,5R)-2-acetyloxy-3,4,5-tribenzoyloxyoxan-2-yl]methyl benzoate
• CAS: 155137-98-7
• 化学式: C₃₆H₃₀O₁₁
• 分子量: 638.628
• InChiKey: ADRJHVDQMZZWGZ-PAPOKCFQSA-N

物化性质

• 沸点：
  740.9±60.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  47
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-O-acetyl-1,3,4,5-tetra-O-benzoyl-β-D-fructopyranose 、 双丙酮半乳糖 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以95%的产率得到1,3,4,5-tetra-O-benzoyl-β-D-fructopyranosyl-(2→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of d-fructopyranosides with 2-O-acyl-β-d-fructopyranosides

  摘要：

  Glycosylation of 2-O-acyl fructopyranosides was investigated, which were shown to be effective glycosyl donors for D-fructopyranoside synthesis with good beta-selectivity and yields. For bulky acceptor 4e, alpha-anomer 5e was obtained with alpha/beta = 65:23. Unexpected ring-opening was observed during acetylation of 9, indicating the sensitivity of the fructopyranosyl ring. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.10.128
• 作为产物：
  描述：

  1,3,4,5-O-tetrabenzoyl-D-fructopyranose 、 乙酸酐 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到2-O-acetyl-1,3,4,5-tetra-O-benzoyl-β-D-fructopyranose
  参考文献：
  名称：

  Efficient D-Fructopyranosylation Method Catalyzed by Scandium Triflate and Preparation of New Sucrose Analogs

  摘要：

  We successfully established a highly efficient beta-fructopyranosylation method that used a fully benzoylated beta-D-fructopyranosyl acetate as the glycosyl donor and Sc(OTf)(3) as the catalytic activator. The syntheses of non-reducing disaccharide units as new sucrose analogs were achieved based on the beta-fructopyranosylation reaction of 1-hydroxy group of glucose derivatives.

  DOI：

  10.3987/com-16-s(s)46

文献信息

• Pyranoid d-fructosyl and l-sorbosyl cyanides
  作者：Frieder W. Lichtenthaler、Frank Hoyer

  DOI：10.1016/0008-6215(94)80061-8

  日期：1994.2

  X-ray structural analysis. From the conformational preferences of the 2-epimers — the cyano group invariably adopts an axial disposition entailing the 5 C 2 conformation for the β- d - fructo and α- l - sorbo cyanides versus the alternative 2 C 5 form for the α- d - fructo and β- l - sorbo anomers — the anomeric effect of a cyano group may be assessed to be of the same order of magnitude as that exerted

  摘要通过使2-O-乙酰基-1,3,4,5-四-O-苯甲酰基衍生物分别与BF 3-三甲基甲硅烷基氰化物在硝基甲烷中反应，制得了端基异-d-呋喃果糖基氰基和1-山梨醇基氰基氰化物。在旋转比较，1 H NMR数据的基础上，以及在X-d-果糖基氰化物的情况下，通过X射线结构分析确定了在第三中心的产物的构型。从2表位分子的构象偏爱出发，氰基始终采用轴向排列，其中β-d-果糖和α-l-山梨醇氰化物的5 C 2构象相对于α-d的替代2 C 5形式。 -果糖和β-1-山梨醇异构体-氰基的异头作用可以评估为与酰氧基官能团相同的数量级。
• Brigl; Schinle, Chemische Berichte, 1933, vol. 66, p. 325,327
  作者：Brigl、Schinle

  DOI：——

  日期：——