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化学学报
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化学学报 ›› 2012, Vol. 70 ›› Issue (11): 1322-1326.DOI: 10.6023/A1112162 上一篇    

研究简报

氟烷磺酰氟和全乙酰基保护的吡喃型半缩醛单糖的氟代反应

严兆华a,b, 赖焜民a, 田伟生b, 余章昕a   

  1. a 南昌大学化学系 南昌 330031;
    b 中国科学院上海有机化学研究所 上海 200032
  • 投稿日期:2011-12-16 修回日期:2012-04-23 发布日期:2012-04-23
  • 通讯作者: 严兆华, 田伟生

Deoxyfluorination of Peracetylated Pyranose Hemiacetal with Fluoroalkanesulfonyl Fluoride

Yan Zhaohuaa,b, Lai Kunmina, Tian Weishengb, Yu Zhangxina   

  1. a Department of Chemistry, Nanchang University, Nanchang 330031;
    b Shanghai Institute of Organic Chemistry, Shanghai 200032
  • Received:2011-12-16 Revised:2012-04-23 Published:2012-04-23

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1167

被引次数

14 | 3

考察了5-氢-3-氧杂-1,1,2,2,4,4,5,5-八氟戊烷磺酰氟(HCF2CF2OCF2CF2SO2F)和全乙酰基保护的吡喃型半缩醛单糖在有机碱存在下的氟代反应. 实验结果表明, 氟烷基磺酰氟试剂HCF2CF2OCF2CF2SO2F 能够诱导全乙酰基保护的吡喃型半缩醛单糖发生氟代反应而生成相应的氟代糖苷, 得率44%～94%. 该方法具有反应条件温和和后处理简便等优点, 可作为一种有效的方法用于氟代糖苷的制备中.

关键词: 5-氢-3-氧杂-1,1,2,2,4,4,5,5-八氟戊烷磺酰氟, 吡喃型半缩醛单糖, 氟代糖苷, 氟代反应

The deoxyfluorination of peracetylated pyranose hemiacetals with 5-H-3-oxa-1,1,2,2,4,4,5,5- octafluoropentanesulfonyl fluoride (HCF2CF2OCF2CF2SO2F) in the presence of an organic base was investigated resulting in the smooth formation of corresponding glycosyl fluorides in the yield of 44%～94%. The mild reaction conditions and easy work-up procedure are the two advantages for this methodology and it can be used as an alternative method for the preparation of glycosyl fluorides.

Key words: 5-H-3-oxa-1,1,2,2,4,4,5,5-octafluoropentanesulfonyl fluoride, pyranose hemiacetal, glycosyl fluoride, deoxyfluorination