methyl 6-O-arachidoyl-α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: methyl 6-O-arachidoyl-α-D-glucopyranoside
• 英文别名: [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl icosanoate
• 化学式: C₂₇H₅₂O₇
• 分子量: 488.706
• InChiKey: IKOGLBNOEALHBT-INFWBLCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  34
• 可旋转键数：
  22
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  二十酸 在 吡啶 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 methyl 6-O-arachidoyl-α-D-glucopyranoside
  参考文献：
  名称：

  A New Highly Regioselective Reaction of Unprotected Sugars for Chemical Synthesis of 6-Acyl-D-Glycopyranosides

  摘要：

  New methodologies developed to synthesize 6-acyl-D-glycopyranosides are described. Thus, regioselective acylation of non protectedglycopyranosides was performed using acyl-p-nitrothiophenol esters and acyl-2,4-dinitrophenol esters as the acylating reagents, yielding 6-acylated derivatives in high yields.

  DOI：

  10.1080/00397919508011779

文献信息

• A New Highly Regioselective Reaction of Unprotected Sugars for Chemical Synthesis of Methyl-6-D-acyl-D-glycopyranosides by Mean of Chlorophosphoric Acid Diethyl Ester[(C₂H₅O)₂P(:O)Cl] as Condensing Reagent
  作者：Jie Xia、Yongzheng Hui

  DOI：10.1080/00397919608003614

  日期：1996.1

  A new methodology which allows the regioselective acylation of no protected methyl-D-glycopyranosides at the primary hydroxy group is described. Thus, a new synthetic procedure is presented to synthesize 6-acyl-methyl-glycopyranosides from unprotected glycopyranosides by means of (EtO)2P:OCl as condensing reagent.