butyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside | 1269489-97-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: butyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside
• 英文别名: N-[(2R,3R,4R,5S,6R)-2-butoxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]acetamide
• CAS: 1269489-97-5
• 化学式: C₃₃H₄₁NO₆
• 分子量: 547.692
• InChiKey: JRLFKKLQDJQFMD-YKNMHBIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  40
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  D-GlcNAc 在 N-氯代丁二酰亚胺 、 sodium acetate 、 sodium hydride 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 butyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Use of N,O-Dimethylhydroxylamine As an Anomeric Protecting Group in Carbohydrate Synthesis

  摘要：

  The N,O-dimethyloxyamine-N-glycosides are introduced as anomerically protected building blocks for carbohydrate synthesis. These N-glycosides are stable to a variety of protecting group manipulations including acylation, alkylation, silylation, and acetal formation. The alkoxyamine-N-glycosides can be cleaved selectively with N-chlorosuccinimide to give the desired hemiacetals in excellent yield. Furthermore, these N-glycosides are stable to the activation conditions required for glycosylation using thioglycoside and trichloroacetimidate glycosyl donors suggesting N,O-dialkoxyamine-N-glycosides will be useful for complex oligosaccharide synthesis.

  DOI：

  10.1021/jo102372m

文献信息

• Use of <i>N</i>,<i>O</i>-Dimethylhydroxylamine As an Anomeric Protecting Group in Carbohydrate Synthesis
  作者：Somnath Dasgupta、Mark Nitz

  DOI：10.1021/jo102372m

  日期：2011.3.18

  The N,O-dimethyloxyamine-N-glycosides are introduced as anomerically protected building blocks for carbohydrate synthesis. These N-glycosides are stable to a variety of protecting group manipulations including acylation, alkylation, silylation, and acetal formation. The alkoxyamine-N-glycosides can be cleaved selectively with N-chlorosuccinimide to give the desired hemiacetals in excellent yield. Furthermore, these N-glycosides are stable to the activation conditions required for glycosylation using thioglycoside and trichloroacetimidate glycosyl donors suggesting N,O-dialkoxyamine-N-glycosides will be useful for complex oligosaccharide synthesis.