A convenient synthesis of derivatives of 3-deoxy-3-fluoro-L-idose
1972; Elsevier BV; Volume: 21; Issue: 2 Linguagem: Inglês
10.1016/s0008-6215(00)82157-6
ISSN1873-426X
AutoresJ. S. Brimacombe, A. M. Mofti, J.H. Westwood,
Tópico(s)Glycosylation and Glycoproteins Research
ResumoThere has been a substantial increase in recent years in the number of fluorinated carbohydrates. One of the reasons for interest in these sugars is that the introduction of a fluorine atom into naturally occurring compounds involved in biochemical processes has, in several instances, produced analogues having significant biological activity and, in some icstances, of therapeutic value’. The most successful ways for specifically introducing a fluorine atom into sugars have used’ (a) nucleophilic displacement of sulphonates with fluoride ion, (6) opening of epoxides, and (c) electrophilic addition of trifluoro(fluoroxy)methane to glycals. Other methods have been applied with less success3. The foregoing procedures have made a number of fluoro sugar derivatives available in quantities sufficient for further transformations to be effected, thereby providing routes to other, less-accessible compounds. Such procedures have been used already in the synthesis of difluoro sugars4, and 3-deoxy-3-fluoro-D-xylose has been prepared5 by a sequence of reactions based on 3-deoxy-3-fluoro-1,2:5,6-di-Oisopropylidene-cc-D-glucofuranose. We now report the conversion of the latter compound into derivatives of 3-deoxy-3-fluoro-L-idose. 3-Deoxy-3-fluoro-1,2:5,6-di-Oisopropylidene-P-L-idofuranose (2) was previously obtained6 by the reaction of tetra-n-butylammonium fluoride in boiling acetonitrile with 1,2:5,6-di-O-isopropylidene-3-0-toluene-p-sulphonyl-/3-L-talofuranose (l), but the route to related derivatives described below is far more convenient.
Referência(s)