benzyl-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside | 112485-12-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
• 英文别名: tri-O-acetyl-3-acetylamino-1-phenyl-D-glycero-D-gulo-2,6-anhydro-1,3-dideoxy-heptitol；Tri-O-acetyl-3-acetylamino-1-phenyl-D-glycero-D-gulo-2,6-anhydro-1,3-didesoxy-heptit
• CAS: 112485-12-8
• 化学式: C₂₁H₂₇NO₈
• 分子量: 421.447
• InChiKey: HVLSBVRQTJKYRX-QGLKVJOYSA-N

物化性质

• 沸点：
  575.3±50.0 °C(predicted)
• 密度：
  1.24±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.93
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  117.23
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  苄基溴化镁 、 3,4,6-tri-O-acetyl-2-amino-2-deoxy-α-D-glucopyranosyl bromide hydrobromide 在 乙醚 作用下， 生成 benzyl-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Yoshimura et al., Nippon Kagaku Zasshi, 1958, vol. 79, p. 1503,1505

  摘要：

  DOI：

文献信息

• The application of the intermediate 2-methyl-glyco-[2,1-d]-2-oxazolines for glycoside synthesis
  作者：Sergey S Pertel、Vasily Ya Chirva、Andrey L Kadun、Elena S Kakayan

  DOI：10.1016/s0008-6215(00)00237-8

  日期：2000.12

  The synthesis of 2-acylamino-2-deoxysugars 1,2-trans-glycosides is described via the oxazolinium salt generated from an O,N-acetylated 1,2cis-glycosyl halide of 2-amino-2-deoxysugar under the conditions of halide-anion catalysis. This salt was then interacted with alcohol to form the corresponding 1,2-trans-glycoside. A method for removing the generated hydrogen chloride is described. The conditions of this synthesis allow glycosides with acid-labile functional groups to be obtained. Suppression of the anomerisation of 1,2-trans-glycosides was achieved by the introduction of N,N'-dicyclohexyl urea into the reaction medium. (C) 2000 Elsevier Science Ltd. All rights reserved.