ORGANOFLUORINE COMPOUNDS AND FLUORINATING AGENTS .15. O-DIFLUOROMETHYLATIONS OF MONOSACCHARIDES BY TRIFLUOROMETHYLZINE BROMIDE

Authors
MIETHCHEN R HEIN M NAUMANN D TYRRA W
Citation
R. Miethchen et al., ORGANOFLUORINE COMPOUNDS AND FLUORINATING AGENTS .15. O-DIFLUOROMETHYLATIONS OF MONOSACCHARIDES BY TRIFLUOROMETHYLZINE BROMIDE, Liebigs Annalen, (9), 1995, pp. 1717-1719
Citations number
24
Categorie Soggetti
Chemistry
Journal title
Liebigs Annalen → ACNP
ISSN journal
09473440
Issue
9
Year of publication
1995
Pages
1717 - 1719
Database
ISI
SICI code
0947-3440(1995):9<1717:OCAFA.>2.0.ZU;2-P
Abstract
,2:3,4-Di-O-isopropylidene-alpha-D-galactopyranose (1), methyl 2,2,2-t richloroethylidene)-alpha-D-altropyranoside (4), methyl ,6-O-benzylide ne-2-O-tosyl-alpha-D-glucopyranoside (6), and methyl 4,6-O-benzylidene -alpha-D-glucopyranoside (8) were O-difluoromethylated with trifluorom ethylzinc bromide (ZnBrCF3 . 2 CH3CN) in a convenient procedure giving the difluoromethyl ethers 2,5,7,9, and the bis(difluoromethyl) ether 10 in moderate yields. The ,2:3,4-di-O-isopropylidene-alpha-D-galactop yranose (2) was deprotected by treatment with aqueous trifluoroacetic acid forming 6-O-difluoromethyl-D-galactopyranose (3).