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Acta Chimica Sinica >

2012 , Vol. 70 >Issue 11: 1322 - 1326

DOI: https://doi.org/10.6023/A1112162

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Deoxyfluorination of Peracetylated Pyranose Hemiacetal with Fluoroalkanesulfonyl Fluoride

  • Yan Zhaohua ,
  • Lai Kunmin ,
  • Tian Weisheng ,
  • Yu Zhangxin
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  • a Department of Chemistry, Nanchang University, Nanchang 330031;
    b Shanghai Institute of Organic Chemistry, Shanghai 200032

Received date: 2011-12-16

  Revised date: 2012-04-23

  Online published: 2012-04-23

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Abstract

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

Cite this article

Yan Zhaohua , Lai Kunmin , Tian Weisheng , Yu Zhangxin . Deoxyfluorination of Peracetylated Pyranose Hemiacetal with Fluoroalkanesulfonyl Fluoride[J]. Acta Chimica Sinica, 2012 , 70(11) : 1322 -1326 . DOI: 10.6023/A1112162

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