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 | 1269490-40-5

• 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-α-L-rhamnopyranosyl-[1->4]-2,3,6-tri-O-acetyl-β-D-glucopyranosyl)hydroxylamine
• 英文别名: [(2R,3R,4S,5R,6R)-4,5-diacetyloxy-6-[methoxy(methyl)amino]-3-[(2S,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 1269490-40-5
• 化学式: C₂₆H₃₉NO₁₆
• 分子量: 621.593
• InChiKey: GIYIWCQSQIEZNU-XZKKFNQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  43
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  198
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  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 在 N-氯代丁二酰亚胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以88%的产率得到2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->4)-2,3,6-tri-O-acetyl-D-glucopyranose
  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-(2,3,6-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