1-hexadecyl 2-hydroxy-3,4,6-tri-O-acetyl-α-D-glucopyranoside | 142789-88-6

• 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: 1-hexadecyl 2-hydroxy-3,4,6-tri-O-acetyl-α-D-glucopyranoside
• 英文别名: cetyl 3,4,6-tri-O-acetyl-α-D-glucopyranoside；[(2R,3R,4R,5R,6S)-3,4-diacetyloxy-6-hexadecoxy-5-hydroxyoxan-2-yl]methyl acetate
• CAS: 142789-88-6
• 化学式: C₂₈H₅₀O₉
• 分子量: 530.7
• InChiKey: ZMEFIXFKDDRDQD-FXGKLIOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  37
• 可旋转键数：
  23
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  1-十六烷醇 、 β-D-葡萄糖五乙酸酯 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 240.0h， 生成 1-hexadecyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 、 1-hexadecyl 2-hydroxy-3,4,6-tri-O-acetyl-α-D-glucopyranoside
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

• Direct Transformation of O-Glycosides into Other O-Glycosides Using Trimethylsilyl Bromide and Zinc Bromide.
  作者：Kunio HIGASHI、Kiyoshi NAKAYAMA、Emiko SHIOYA、Tsuneo KUSAMA

  DOI：10.1248/cpb.40.1042

  日期：——

  We have succeeded in developing a novel glycosidation catalyzed by a combination of trimethylsilyl bromide (TMSBr) and a Lewis acid using simple O-glycosides as glycosyl donors. Treatment of benzyl 2-deozy-2-tri-chloroethoxycarbonylamino-D-glucopyranoside with TMSBr and zinc bromide in the presence of glycosyl acceptors gave α-O-glycosides in moderate to high yields. Zinc triflate and tin(II)triflate were also found to be effective as the Lewis acid. This new methodology is applicable to methyl D-glucopyranoside.

  我们成功开发了一种新型的糖苷化反应，该反应是由三甲基氯化铵（TMSBr）和路易斯酸的组合催化，使用简单的O-糖苷作为糖苷供体。将苄基2-脱氧-2-三氯乙氧羧酰胺-D-葡萄糖吡喃糖苷与TMSBr和溴化锌在糖苷受体存在下处理，获得了中到高产率的α-O-糖苷。此外，三氟甲苯酸锌和亚锡三氟甲苯酸也被发现作为路易斯酸有效。该新方法适用于甲基D-葡萄糖吡喃糖苷。
• Konstantinovic; Predojevic; Mojsilovic, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 9, p. 796 - 801
  作者：Konstantinovic、Predojevic、Mojsilovic、Dimitrijevic、Milosevic

  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.