octyl 3,4,6-tri-O-acetyl-α-D-glucopyranoside | 143206-84-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: octyl 3,4,6-tri-O-acetyl-α-D-glucopyranoside
• 英文别名: [(2R,3R,4R,5R,6S)-3,4-diacetyloxy-5-hydroxy-6-octoxyoxan-2-yl]methyl acetate
• CAS: 143206-84-2
• 化学式: C₂₀H₃₄O₉
• 分子量: 418.485
• InChiKey: WVIUGITYDPXFDE-WAPOTWQKSA-N

物化性质

• 沸点：
  501.8±50.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  29
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 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：

  phenyl 3,4,6-tri-O-acetyl-α-D-gluco-1-thiopyranoside 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 octyl 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

• Petrovic, Zorica; Konstantinovic, Stanimir; Spasojevic, Aleksandra, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 1, p. 132 - 134
  作者：Petrovic, Zorica、Konstantinovic, Stanimir、Spasojevic, Aleksandra

  DOI：——

  日期：——
• Zeolite-catalyzed Helferich-type glycosylation of long-chain alcohols. Synthesis of acetylated alkyl 1,2-trans glycopyranosides and alkyl 1,2-cis C2-hydroxy-glycopyranosides
  作者：Udayanath Aich、Duraikkannu Loganathan

  DOI：10.1016/j.carres.2006.12.014

  日期：2007.4

  Zeolite-catalyzed glycosylation of long-chain alcohols, using the inexpensive and readily available peracetylated beta-D-gluco- and galactopyranoses as glycosyl donors under solvent free conditions, has been explored for the first time. Among the various forms (H-, Na-, Fe- and Zn) of beta zeolite examined as catalysts in the reaction of 1,2,3,4,6-penta-O-acetyl-beta-D-galactopyranose with cetyl alcohol, Fe-beta zeolite gave the maximum yield of 63% of cetyl 2,3,4,6-tetra-O-acetyl-p-D-galactopyranoside and cetyl 3,4,6-tri-O-acetyl-alpha-D-galactopyranoside. Fe-beta Zeolite-catalyzed glycosylation was found to be general affording the title compounds in each case in a moderate yield, but with a good stereoselectivity. The yield of synthetically valuable acetylated long-chain alkyl 1,2-cis C2-hydroxy-glycopyranosides obtained in the present single-step procedure is considerably higher than that of the previously reported multi-step method employing the Stork silicon tether approach. (c) 2006 Elsevier Ltd. All rights reserved.
• Bols, Mikael, Acta Chemica Scandinavica, 1993, vol. 47, # 8, p. 829 - 834
  作者：Bols, Mikael

  DOI：——

  日期：——