N,O-dimethyl-N-(4,6-O-benzylidene-β-D-glucopyranosyl)hydroxylamine | 1269490-06-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N,O-dimethyl-N-(4,6-O-benzylidene-β-D-glucopyranosyl)hydroxylamine
• 英文别名: (2R,4aR,6R,7R,8R,8aS)-6-[methoxy(methyl)amino]-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS: 1269490-06-3
• 化学式: C₁₅H₂₁NO₆
• 分子量: 311.335
• InChiKey: BGLSKXBQIOATFC-BXLXJSPXSA-N

物化性质

• 沸点：
  486.3±55.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N,O-dimethyl-N-(4,6-O-benzylidene-β-D-glucopyranosyl)hydroxylamine 在 三甲基氯硅烷 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 以81%的产率得到4,6-O-benzylidene-D-glucose
  参考文献：
  名称：

  A New Method for Selective Deprotection of AnomericN,O-Dimethylhydroxylamine Promoted by TMSCl

  摘要：

  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.

  DOI：

  10.1080/07328303.2012.762104
• 作为产物：
  描述：

  可得然胶 在 sodium acetate 、 对甲苯磺酸 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 生成 N,O-dimethyl-N-(4,6-O-benzylidene-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