methyl 6-azido-4-O-benzoyl-6-deoxy-2,3-di-O-methyl-α-D-glucopyranoside | 1054604-11-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-azido-4-O-benzoyl-6-deoxy-2,3-di-O-methyl-α-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-2-(azidomethyl)-4,5,6-trimethoxyoxan-3-yl] benzoate
• CAS: 1054604-11-3
• 化学式: C₁₆H₂₁N₃O₆
• 分子量: 351.359
• InChiKey: SQIGKQDPBBTROL-SSZWKKLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  77.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 6-azido-4-O-benzoyl-6-deoxy-2,3-di-O-methyl-α-D-glucopyranoside 在 三氟甲磺酸酐 、 sodium methylate 、 三苯基膦 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 methyl 4-benzylamino-4,6-dideoxy-2,3-di-O-methyl-6-(N'-phenyl)thioureido-α-D-galactopyranoside
  参考文献：
  名称：

  Preparation of new type of organocatalysts having a carbohydrate scaffold

  摘要：

  The synthesis of nine new, bifunctional organocatalysts having carbohydrate scaffolds has been accomplished. In these catalysts both of the catalytic amino and thiourea functions are directly attached to a carbohydrate core. The activities of the newly prepared catalysts were tested in a Michael addition. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.12.026
• 作为产物：
  描述：

  methyl 4-O-benzoyl-6-bromo-6-deoxy-2,3-di-O-methyl-α-D-glucopyranoside 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以94%的产率得到methyl 6-azido-4-O-benzoyl-6-deoxy-2,3-di-O-methyl-α-D-glucopyranoside
  参考文献：
  名称：

  Preparation of new type of organocatalysts having a carbohydrate scaffold

  摘要：

  The synthesis of nine new, bifunctional organocatalysts having carbohydrate scaffolds has been accomplished. In these catalysts both of the catalytic amino and thiourea functions are directly attached to a carbohydrate core. The activities of the newly prepared catalysts were tested in a Michael addition. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.12.026

文献信息

• Synthesis and application of novel carbohydrate-based ammonium and triazolium salts
  作者：Tamás Nemcsok、Zsolt Rapi、Péter Bagi、Péter Bakó

  DOI：10.1080/00397911.2019.1625403

  日期：2019.9.17

  Abstract The synthesis of nine new carbohydrate-based quaternary ammonium salts and two new triazolium salts starting from d-glucose has been accomplished. Our synthesis utilized the regio- and stereoselective ring opening reaction of 2,3-anhydro sugars by nucleophilic reagents to afford the key intermediates. In these new types of phase transfer catalysts, the ammonium and triazolium functions are

  摘要 已完成以d-葡萄糖为原料合成九种新型碳水化合物基季铵盐和两种新型三唑鎓盐。我们的合成利用亲核试剂对 2,3-脱水糖的区域选择性和立体选择性开环反应来提供关键中间体。在这些新型相转移催化剂中，铵和三唑鎓功能直接连接到碳水化合物支架的不同位置（糖的 2-、3-、6-位）。在 N-（二苯基）亚甲基甘氨酸叔丁酯与苄基溴的烷基化中测试了基于 altrose 和葡萄糖的季盐的效率。据我们所知，这是糖基季铵盐或三唑鎓盐成功用作相转移催化剂的第一个例子。还通过 19 F NMR 光谱研究了合成盐对外消旋 Mosher 酸性银盐的对映体识别能力。图形概要
• Preparation of new type of organocatalysts having a carbohydrate scaffold
  作者：Károly Ágoston、Péter Fügedi

  DOI：10.1016/j.carres.2013.12.026

  日期：2014.5

  The synthesis of nine new, bifunctional organocatalysts having carbohydrate scaffolds has been accomplished. In these catalysts both of the catalytic amino and thiourea functions are directly attached to a carbohydrate core. The activities of the newly prepared catalysts were tested in a Michael addition. (C) 2014 Elsevier Ltd. All rights reserved.