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Acta Chimica Sinica ›› 2012, Vol. 70 ›› Issue (11): 1322-1326.DOI: 10.6023/A1112162 Previous Articles    

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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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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