2,3-epoxypropyl 2-acetamido-2-deoxy-β-D-glucopyranoside | 28738-50-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-epoxypropyl 2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: N-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(oxiran-2-ylmethoxy)oxan-3-yl]acetamide
• CAS: 28738-50-3
• 化学式: C₁₁H₁₉NO₇
• 分子量: 277.274
• InChiKey: ZLBOPFHCWHMRFS-MSSAAIDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  121
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,3-epoxypropyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 在 magnesium oxide 作用下， 以 甲醇 为溶剂， 反应 80.0h， 以52%的产率得到2,3-epoxypropyl 2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Syntheses of spacer-armed carbohydrate model compounds

  摘要：

  Commercially available chemicals, such as diethylene glycol, 1,9-nonanediol, 9-decen-1-ol, 1,2,6-hexanetriol, and p-nitrophenol were used to prepare spacer-armed carbohydrate derivatives. Glycosides of D-glucose, N-acetyl-D-glucosamine and 3-O-methyl-D-glucose have been synthesized, carrying reactive groups at the end of the spacer-arms. These glycosides are capable of forming neoglycoproteins. When bromo sugars were reacted with highly apolar aglycones in the presence of mercuric cyanide or mercuric bromide, a considerable amount of '2-OH-compounds' (such as 9-hydroxynonyl 3,4,6-tri-O-acetyl-beta-D-glucopyranoside) were formed. Some spacer-armed derivatives (such as 9,10-epoxydecyl beta-D-glucopyranoside) are theoretically a mixture of diastereomers, but this fact does not mirror in the H-1 and C-13 NMR spectra. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00256-x