1-O-(4,4,5,5,6,6,7,7,7-nonafluoro-2-hydroxyheptyl)-DL-xylitol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-(4,4,5,5,6,6,7,7,7-nonafluoro-2-hydroxyheptyl)-DL-xylitol
• 英文别名: (2R,3S,4S)-5-(4,4,5,5,6,6,7,7,7-nonafluoro-2-hydroxyheptoxy)pentane-1,2,3,4-tetrol
• 化学式: C₁₂H₁₇F₉O₆
• 分子量: 428.249
• InChiKey: QFIVWUFKPWPUMR-HOGRAUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  Xylitol 在 氢气 、 三氟乙酸 作用下， 以 水 为溶剂， 反应 10.5h， 生成 1-O-(4,4,5,5,6,6,7,7,7-nonafluoro-2-hydroxyheptyl)-DL-xylitol
  参考文献：
  名称：

  Novel perfluoroalkylated derivatives of d-galactopyranose and xylitol for biomedical uses. Hemocompatibility and effect on perfluorocarbon emulsions

  摘要：

  6-O-(4,4,5,5,6,6,7,7,7-Nonafluoro-2-hydroxyheptyl)-, 6-O-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-hydroxynonyl)-, and 6-O-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-2-hydroxyundecyl)-D-galactopyranose (9, 10, and 11, resp.) were prepared by a two-step synthesis including the reaction of 1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose with 2-[(perfluoroalkyl)methyl]oxiranes under catalysis with BF3.Et2O. Similarly, 1-O-(4,4,5,5,6,6,7,7,7-nonafluoro-2-hydroxyheptyl)-, 1-O-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-hydroxynonyl)-, 1-O-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-2-hydroxyundecyl)-DL-xylitol (18, 19, and 20, resp.) were prepared by a two-step synthesis from the corresponding 1,2:3,4-di-O-isopropylidene-DL-xylitol. Most of the both types of fluoroalkylated carbohydrate derivatives 9-11 and 18-20 generally displayed very low level of hemolytic activity and excellent co-emulsifying properties on testing on perfluorodecalin-Pluronic F-68 microemulsions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.06.019

文献信息

• Novel perfluoroalkylated derivatives of d-galactopyranose and xylitol for biomedical uses. Hemocompatibility and effect on perfluorocarbon emulsions
  作者：Vladimı́r Cı́rkva、Radek Polák、Oldřich Paleta、Karel Kefurt、Jitka Moravcová、Milan Kodı́ček、Stanislav Forman

  DOI：10.1016/j.carres.2004.06.019

  日期：2004.9

  6-O-(4,4,5,5,6,6,7,7,7-Nonafluoro-2-hydroxyheptyl)-, 6-O-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-hydroxynonyl)-, and 6-O-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-2-hydroxyundecyl)-D-galactopyranose (9, 10, and 11, resp.) were prepared by a two-step synthesis including the reaction of 1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose with 2-[(perfluoroalkyl)methyl]oxiranes under catalysis with BF3.Et2O. Similarly, 1-O-(4,4,5,5,6,6,7,7,7-nonafluoro-2-hydroxyheptyl)-, 1-O-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-hydroxynonyl)-, 1-O-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-2-hydroxyundecyl)-DL-xylitol (18, 19, and 20, resp.) were prepared by a two-step synthesis from the corresponding 1,2:3,4-di-O-isopropylidene-DL-xylitol. Most of the both types of fluoroalkylated carbohydrate derivatives 9-11 and 18-20 generally displayed very low level of hemolytic activity and excellent co-emulsifying properties on testing on perfluorodecalin-Pluronic F-68 microemulsions. (C) 2004 Elsevier Ltd. All rights reserved.