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Organofluorine compounds and fluorinating agents, 15. O ‐difluoromethylations of monosaccharides by trifluoromethylzinc bromide
Author(s) -
Miethchen Ralf,
Hein Martin,
Naumann Dieter,
Tyrra Wieland
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.1995199509241
Subject(s) - chemistry , bromide , monosaccharide , ether , aqueous solution , pyranose , medicinal chemistry , stereochemistry , organic chemistry
1,2:3,4‐Di‐ O ‐isopropylidene‐α‐ D ‐galactopyranose ( 1 ), methyl 2‐ O ‐(cyclohexylcarbamoyl)‐3,4‐ O ‐(2,2,2‐ trichloroethylidene)‐α‐ D ‐altropyranoside ( 4 ), methyl 4,6‐ O ‐benzylidene‐2‐ O ‐to‐syl‐α‐ D ‐glucopyranoside ( 6 ), and methyl 4,6‐ O ‐benzylidene‐α‐ D ‐glucopyranoside ( 8 ) were O ‐difluoromethylated with tri‐fluoromethylzinc bromide (ZnBrCF 3 . 2 CH 3 CN) in a convenient procedure giving the difluoromethyl ethers 2, 5, 7, 9 , and the bis(difluoromethyl) ether 10 in moderate yields. The 6‐ O ‐difluoromethyl‐1,2:3,4‐di‐ O ‐isopropylidene‐ α‐ D ‐galacto‐pyranose ( 2 ) was deprotected by treatment with aqueous tri‐fluoroacetic acid forming 6‐ O ‐difluoromethyl‐ D ‐galactopyranose ( 3 ).