N,O-dimethyl-N-(2,3,4,6 tetra-O-acetyl-β-D-glucopyranosyl)hydroxylamine | 1269489-99-7

• 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-(2,3,4,6 tetra-O-acetyl-β-D-glucopyranosyl)hydroxylamine
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[methoxy(methyl)amino]oxan-2-yl]methyl acetate
• CAS: 1269489-99-7
• 化学式: C₁₆H₂₅NO₁₀
• 分子量: 391.375
• InChiKey: YMQHOAZFGUGXMA-IBEHDNSVSA-N

物化性质

• 沸点：
  430.0±55.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  127
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  N,O-dimethyl-N-(2,3,4,6 tetra-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91%的产率得到2,3,4,5-tetra-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：

  可得然胶 在 吡啶 、 sodium acetate 作用下， 以 水 为溶剂， 反应 1.0h， 生成 N,O-dimethyl-N-(2,3,4,6 tetra-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

文献信息

• A New Method for Selective Deprotection of Anomeric<i>N,O</i>-Dimethylhydroxylamine Promoted by TMSCl
  作者：Shengjun Huang、Jun Liao、Qingjie Zhao、Xiaoyun Chai、Baogang Wang、Shichong Yu、Qiuye Wu

  DOI：10.1080/07328303.2012.762104

  日期：2013.2.12

  TMSCl was shown to be an efficient reagent for selective deprotection of the anomeric position protected as N, O-dimethylhydroxylamine glycoside. This deprotection condition was proved to be compatible with a number of protecting groups, such as the TB-DPS, acetyl, benzyl, benzylidene, and benzoyl groups.