phenyl 3,4,6-tri-O-acetyl-α-D-glucopyranoside | 143206-88-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3,4,6-tri-O-acetyl-α-D-glucopyranoside
• 英文别名: [(2R,3R,4R,5R,6R)-3,4-diacetyloxy-5-hydroxy-6-phenoxyoxan-2-yl]methyl acetate
• CAS: 143206-88-6
• 化学式: C₁₈H₂₂O₉
• 分子量: 382.367
• InChiKey: XLWSODGJYJZMJC-ZKXLYKBJSA-N

物化性质

• 沸点：
  502.5±50.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-β-D-glucopyranosyl chloride 在 吡啶 、 N-碘代丁二酰亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.17h， 生成 phenyl 3,4,6-tri-O-acetyl-α-D-glucopyranoside
  参考文献：
  名称：

  Stereocontrolled synthesis of α-glucosides by intramolecular glycosidation

  摘要：

  α-葡萄糖苷是通过将苯硫基 3,4,6-三-O-乙酰基-α-D-吡喃葡萄糖苷和醇或酚与二甲基甲硅烷基桥连接，然后进行碘鎓离子催化的分子内糖苷化来制备的。

  DOI：

  10.1039/c39920000913

文献信息

• Stereoselective single-step synthesis and X-ray crystallographic investigation of acetylated aryl 1,2-trans glycopyranosides and aryl 1,2-cis C2-hydroxy-glycopyranosides
  作者：Udayanath Aich、Duraikkannu Loganathan

  DOI：10.1016/j.carres.2005.10.010

  日期：2006.1

  Reported is an attractive and environmentally friendly method for the synthesis of the title compounds in moderate yield using inexpensive 1,2,3,4,6-penta-O-acetyl-beta-D-gluco- and galactopyranoses as sugar donors, five different phenols as acceptors and H-beta zeolite as the catalyst. The yield (23-28%) of aryl 3,4,6-tri-O-acetyl-alpha-D-glycopyranosides obtained in this single-step procedure is considerably higher than that obtained using previously reported methods. Treatment of an orthoacetate, 3,4,6-tri-O-acetyl-[1,2-O-(1-p-fluorophenoxyethylidene)]-alpha-D-glucopyranose, with p-fluorophenol under the same solvent-free reaction conditions also led to the formation of the title compounds in similar yield and composition. X-ray crystallographic analysis of phenyl 3,4,6-tri-O-acetyl-alpha-D-glucopyranoside and p-fluorophenyl 3,4,6-tri-O-acetyl-alpha-D-glucopyranoside showed that the molecular packing is stabilized by C-H center dot center dot center dot O, C-H center dot center dot center dot pi and C-H center dot center dot center dot F interactions, in addition to regular hydrogen bonding patterns. (c) 2005 Elsevier Ltd. All rights reserved.
• Bols, Mikael, Acta Chemica Scandinavica, 1993, vol. 47, # 8, p. 829 - 834
  作者：Bols, Mikael

  DOI：——

  日期：——