N,O-dimethyl-N-(β-D-glucopyranosyl)hydroxylamine

• 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-(β-D-glucopyranosyl)hydroxylamine
• 英文别名: N-Methoxy-N-methyl-beta-D-glucopyranosylamine；(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[methoxy(methyl)amino]oxane-3,4,5-triol
• 化学式: C₈H₁₇NO₆
• 分子量: 223.226
• InChiKey: CEYYBXHCZIZBGB-JAJWTYFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  103
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N,O-dimethyl-N-(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93%的产率得到D-葡萄糖
  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 、 二甲羟胺盐酸盐 在 sodium acetate 作用下， 以 水 为溶剂， 以92%的产率得到N,O-dimethyl-N-(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

• TBAF Effects 3,6-Anhydro Formation from 6-<i>O</i>-Tosyl Pyranosides
  作者：Zachary A. Morrison、Mark Nitz

  DOI：10.1021/acs.orglett.0c00045

  日期：2020.2.21

  3,6-Anhydro sugars are common structures in algal polysaccharides and occur in the furanodictine and sauropunol natural products. We have found that treatment of 6-O-tosylpyranosides with tetrabutylammonium fluoride provides a mild, high-yielding synthesis of 3,6-anhydro sugars. Using O-glycoside substrates, 3,6-anhydropyranosides are isolated and the use of N,O-dimethyl hydroxylamine glycosides yields

  3,6-脱水糖是藻类多糖中的常见结构，并存在于呋喃达克丁和sauropunol天然产物中。我们发现用氟化四丁基铵处理6-O-甲苯磺酰基吡喃糖苷提供了温和的，高产率的3，6-脱水糖的合成。使用O-糖苷底物，分离出3，6-脱水吡喃糖苷，并且使用N，O-二甲基羟胺糖苷产生3，6-脱水呋喃糖苷。据报道，采用这种方法，可以合成几种3,6-脱水糖天然产物的简捷合成路线，包括呋喃果苦碱A和sauropunols AD。
• Chemo- and stereoselective glycosylation of hydroxylamino derivatives: A versatile approach to glycoconjugates
  作者：Francesco Peri、Pascal Dumy、Manfred Mutter

  DOI：10.1016/s0040-4020(98)00763-7

  日期：1998.10

  A general method for the stereoselective coupling of unprotected oligosaccharides with any substrate containing a N,O-disubstituted hydroxylamine group is described. The cyclic nature of the oligosaccharide reducing unit is preserved and the substrate glycosylated with high diastereoselectivity to sugar through an amino (N[OR2]-) or an aminoxy (N[R-1]-O-) linkage. Due to the uniquely high chemical reactivity and specificity of disubstituted hydroxylamine toward the sugar reducing end, neither protecting groups nor activation methods are required to perform the reaction in aqueous solution. The characteristic features and the scope of this new type of glycosylation reaction are exemplified for the chemoselective synthesis of model glycopeptides. (C) 1998 Elsevier Science Ltd. All rights reserved.
• 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.