N,O-dimethyl-N-(2,3,4,6 tetra-O-benzyl-β-D-glucopyranosyl)hydroxylamine | 1269490-02-9

• 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-(2,3,4,6 tetra-O-benzyl-β-D-glucopyranosyl)hydroxylamine
• 英文别名: (2R,3R,4S,5R,6R)-N-methoxy-N-methyl-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-amine
• CAS: 1269490-02-9
• 化学式: C₃₆H₄₁NO₆
• 分子量: 583.725
• InChiKey: HKFYHZJLIULBQC-SQGINLDNSA-N

物化性质

• 沸点：
  672.3±65.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于二氯甲烷；DMF；乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N,O-dimethyl-N-(2,3,4,6 tetra-O-benzyl-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90%的产率得到2,3,4,6-四苄基-D-吡喃葡萄糖
  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：

  溴甲苯 、 N,O-dimethyl-N-(β-D-glucopyranosyl)hydroxylamine 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以92%的产率得到N,O-dimethyl-N-(2,3,4,6 tetra-O-benzyl-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.
• Use of <i>N</i>,<i>O</i>-Dimethylhydroxylamine As an Anomeric Protecting Group in Carbohydrate Synthesis
  作者：Somnath Dasgupta、Mark Nitz

  DOI：10.1021/jo102372m

  日期：2011.3.18

  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.