N,O-dimethyl-N-(2,3,4-tri-O-acetyl-6-O-tert-butyl-diphenylsilyl-β-D-glucopyranosyl)hydroxylamine | 1269490-27-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N,O-dimethyl-N-(2,3,4-tri-O-acetyl-6-O-tert-butyl-diphenylsilyl-β-D-glucopyranosyl)hydroxylamine
• 英文别名: [(2R,3R,4S,5R,6R)-4,5-diacetyloxy-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-6-[methoxy(methyl)amino]oxan-3-yl] acetate
• CAS: 1269490-27-8
• 化学式: C₃₀H₄₁NO₉Si
• 分子量: 587.742
• InChiKey: GFBUNAMMBSTMPM-XYPQWYOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  41
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N,O-dimethyl-N-(2,3,4-tri-O-acetyl-6-O-tert-butyl-diphenylsilyl-β-D-glucopyranosyl)hydroxylamine 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 以55%的产率得到N,O-dimethyl-N-(2,3,4-tri-O-acetyl-β-D-glucopyranosyl)hydroxylamine
  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
• 作为产物：
  描述：

  N,O-dimethyl-N-(β-D-glucopyranosyl)hydroxylamine 在 吡啶 作用下， 反应 5.0h， 生成 N,O-dimethyl-N-(2,3,4-tri-O-acetyl-6-O-tert-butyl-diphenylsilyl-β-D-glucopyranosyl)hydroxylamine
  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