allyl 3,4-di-O-acetyl-6-azido-2,6-dideoxy-2-[(trifluoroacetyl)amino]-β-D-glucopyranoside | 365563-81-1

• 分子结构分类: 有机化合物
• 英文名称: allyl 3,4-di-O-acetyl-6-azido-2,6-dideoxy-2-[(trifluoroacetyl)amino]-β-D-glucopyranoside
• 英文别名: allyl 3,4-di-O-acetyl-6-azido-2,6-dideoxy-2-trifluoroacetamido-β-D-glucopyranoside；[(2R,3R,4R,5R,6R)-4-acetyloxy-2-(azidomethyl)-6-prop-2-enoxy-5-[(2,2,2-trifluoroacetyl)amino]oxan-3-yl] acetate
• CAS: 365563-81-1
• 化学式: C₁₅H₁₉F₃N₄O₇
• 分子量: 424.334
• InChiKey: RTAJDYGZLZRBRO-SYLRKERUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  allyl 3,4-di-O-acetyl-6-azido-2,6-dideoxy-2-[(trifluoroacetyl)amino]-β-D-glucopyranoside 在 sodium cyanoborohydride 、 臭氧 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 2-(N-(t-butoxycarbonyl)piperazino)ethyl 3,4-di-O-acetyl-6-azido-2,6-dideoxy-2-trifluoroacetamido-β-D-glucopyranoside
  参考文献：
  名称：

  Parallel synthesis of a small library of novel aminoglycoside analogs based on 2-amino-2-deoxy-d-glucose and d-ribose scaffolds

  摘要：

  The synthesis of a small library of aminoglycoside analogues based on 2-amino-2-deoxy-D-glucose and D-ribose was achieved using reductive amination reactions as key transformations. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00584-1
• 作为产物：
  描述：

  allyl 3,4-di-O-acetyl-2-deoxy-2-trifluoroacetamido-6-O-tosyl-β-D-glucopyranoside 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以76%的产率得到allyl 3,4-di-O-acetyl-6-azido-2,6-dideoxy-2-[(trifluoroacetyl)amino]-β-D-glucopyranoside
  参考文献：
  名称：

  Parallel synthesis of a small library of novel aminoglycoside analogs based on 2-amino-2-deoxy-d-glucose and d-ribose scaffolds

  摘要：

  The synthesis of a small library of aminoglycoside analogues based on 2-amino-2-deoxy-D-glucose and D-ribose was achieved using reductive amination reactions as key transformations. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00584-1

文献信息

• A short route for the synthesis of “sweet” macrocycles via a click-dimerization–ring-closing metathesis approach
  作者：Simon Dörner、Bernhard Westermann

  DOI：10.1039/b502682b

  日期：——

  A facile and flexible approach for the preparation of macrocyclic molecules containing different carbohydrate moieties is presented, employing the reaction cascade: click-dimerization and ring-closing metathesis.

  本文介绍了一种简便灵活的方法，利用级联反应：单击二聚化和闭环偏析，制备含有不同碳水化合物分子的大环分子。