2,3-epoxypropyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside | 28738-47-8

• 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-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-(oxiran-2-ylmethoxy)oxan-2-yl]methyl acetate
• CAS: 28738-47-8
• 化学式: C₁₇H₂₅NO₁₀
• 分子量: 403.386
• InChiKey: QQEDRHRTHBFRBT-MJHKDLPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  139
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  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

文献信息

• Stereoselective synthesis of epoxyalkyl glycoside precursors of glycosyl glycerol analogues from alkenyl glycosides of N-acetyl-d-glucosamine derivatives
  作者：José M. Vega-Pérez、José I. Candela、Eugenia Blanco、Fernando Iglesias-Guerra

  DOI：10.1016/s0957-4166(02)00649-3

  日期：2002.11

  The synthesis of epoxyalkyl glycoside derivatives of N-acetyl-D-glucosamine is described. Epoxidation of the corresponding alkenyl glycosides with m-CPBA took place with different stereoselectivity depending on the nature of the unsaturated system and the protecting groups on the sugar moiety. The configuration of the newly formed stereogenic centres has been confirmed unequivocally by chemical correlation. (C) 2002 Elsevier Science Ltd. All rights reserved.