1-n-tetradecanoyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside

• 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-n-tetradecanoyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] tetradecanoate
• 化学式: C₄₈H₆₂O₇
• 分子量: 751.016
• InChiKey: UOHUONGYGPKSSA-WQNHLRALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.8
• 重原子数：
  55
• 可旋转键数：
  27
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,3,4,6-四苄基-D-吡喃葡萄糖 、 肉豆蔻酸 在 2,4,6-三叔丁基吡啶 、 二甲基硫 、 三氟甲磺酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 9.5h， 生成 1-n-tetradecanoyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 、 1-n-tetradecanoyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Sulfide-Mediated Dehydrative Glycosylation

  摘要：

  The development of a new method for glycosylation with 1-hydroxy glycosyl donors employing dialkyl sulfonium reagents is described. The process employs the reagent combination of a dialkyl sulfide and triflic anhydride to effect anomeric bond constructions. This controlled dehydrative coupling of various C(1)-hemiacetal glycosyl donors and nucleophilic acceptors proceeds by way of a sulfide-to-sulfoxide oxidation process in which triflic anhydride serves as the oxidant.

  DOI：

  10.1021/ja015968p

文献信息

• Sulfide-Mediated Dehydrative Glycosylation
  作者：Hien M. Nguyen、Yanning Chen、Sergio G. Duron、David Y. Gin

  DOI：10.1021/ja015968p

  日期：2001.9.1

  The development of a new method for glycosylation with 1-hydroxy glycosyl donors employing dialkyl sulfonium reagents is described. The process employs the reagent combination of a dialkyl sulfide and triflic anhydride to effect anomeric bond constructions. This controlled dehydrative coupling of various C(1)-hemiacetal glycosyl donors and nucleophilic acceptors proceeds by way of a sulfide-to-sulfoxide oxidation process in which triflic anhydride serves as the oxidant.