TRIFLUOROMETHYLATION OF SUGAR 1,4-LACTONES - SYNTHESIS OF 5-DEOXY-5,5,5-TRIFLUORO-D AND L-RIBOSE AND LYXOSE DERIVATIVES

Authors
MUNIER P PICQ D ANKER D
Citation
P. Munier et al., TRIFLUOROMETHYLATION OF SUGAR 1,4-LACTONES - SYNTHESIS OF 5-DEOXY-5,5,5-TRIFLUORO-D AND L-RIBOSE AND LYXOSE DERIVATIVES, Tetrahedron letters, 34(51), 1993, pp. 8241-8244
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
51
Year of publication
1993
Pages
8241 - 8244
Database
ISI
SICI code
0040-4039(1993)34:51<8241:TOS1-S>2.0.ZU;2-4
Abstract
The four 5-deoxy-5,5,5-trifluoro-D and L-ribo and -lyxo furanoses were synthesized from lactones using CF(3)SiMe(3) in 5 or 6 steps and 30-4 0 % overall yield. The key step was a stereoselective reduction of 1,1 ,1-trifluoror-2-ketoses with LialH(4) or NaBH4 at an anomeric centre.