N,O-dimethyl-N-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)hydroxylamine | 1269490-30-3

• 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-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)hydroxylamine
• 英文别名: [(2R,3R,4S,5R,6R)-4,5-diacetyloxy-3-hydroxy-6-[methoxy(methyl)amino]oxan-2-yl]methyl acetate
• CAS: 1269490-30-3
• 化学式: C₁₄H₂₃NO₉
• 分子量: 349.338
• InChiKey: ZGXOPAPCIGKSLW-RKQHYHRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N,O-dimethyl-N-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)hydroxylamine 、 乙基 2,3,4-三-O-乙酰基-6-脱氧-1-硫代-alpha-L-吡喃甘露糖苷 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以85%的产率得到N,O-dimethyl-N-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-[1->4]-2,3,6-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-(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