2,2,2-trifluoro-1-phenylethyl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside | 1417450-17-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,2,2-trifluoro-1-phenylethyl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside
• CAS: 1417450-17-9
• 化学式: C₁₈H₁₉F₃O₆
• 分子量: 388.34
• InChiKey: LSDFSKFUWRGOKH-TVXGVJEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  1-苯基-2,2,2-三氟乙醇 、 乙酰化葡萄烯糖 在 triflic acid supported on silica gel 作用下， 反应 0.42h， 以50%的产率得到
  参考文献：
  名称：

  CF3SO3H–SiO2 as catalyst for Ferrier rearrangement: an efficient procedure for the synthesis of pseudoglycosides

  摘要：

  An efficient method for the conversion of 2,4,6-tri-O-acetyl-D-glucal to 2,3-unsaturated glycosides by using triflic acid on SiO2 as catalyst has been established. A series of 2,3-unsaturated glucosides were synthesized in good yield and high anomeric selectivity under transition metal-free conditions. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.11.019

文献信息

• An efficient procedure for the synthesis of 2,3-unsaturated-O-glycosides: TiCl3(OTf) as the catalyst for type I Ferrier rearrangement
  作者：Peiran Chen、Lei Lin

  DOI：10.1016/j.tet.2013.04.051

  日期：2013.6

  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.