2,2,2-tri(bromomethyl)ethyl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside | 1432744-70-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2,2,2-tri(bromomethyl)ethyl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside
• CAS: 1432744-70-1
• 化学式: C₁₅H₂₁Br₃O₆
• 分子量: 537.04
• InChiKey: HXTDYOPLBZYSKH-BFHYXJOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  24.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  三溴新戊醇 、 乙酰化葡萄烯糖 在 trichloro(trifluoromethanesulfonato)titanium(IV) 作用下， 以 二氯甲烷 为溶剂， 反应 1.42h， 以66.667%的产率得到
  参考文献：
  名称：

  An efficient procedure for the synthesis of 2,3-unsaturated-O-glycosides: TiCl3(OTf) as the catalyst for type I Ferrier rearrangement

  摘要：

  An efficient type I Ferrier rearrangement reaction system for the synthesis of 2,3-unsaturated-O-glycosides has been established by using TiCl3(OTf) as the catalyst. A series of 2,3-unsaturated-O-glucosides were prepared from 3,4,6-tri-O-acetyl-D-glucal in good yield and high anomeric selectivity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.051

文献信息

• RuCl3·3H2O as catalyst for Ferrier rearrangement: an efficient procedure for the preparation of pseudoglycosides
  作者：Peiran Chen、Lei Lin

  DOI：10.1016/j.tet.2013.09.061

  日期：2013.11

  By using RuCl3 center dot 3H(2)O as catalyst, an improved method for the synthesis of 2,3-unsaturated-glycosides has been established. A series of 2, 3-unsaturated-glucosides were obtained from 2,4,6-tri-O-acetyl-D-glucal or 3,4-di-O-acetyl-6-deoxy-L-glucal in good yield and high anomeric selectivity. (C) 2013 Elsevier Ltd. All rights reserved.