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A New Method for the Selective Introduction of Difluoromethyl and Trifluoromethyl Groups into Sugar Moieties
Author(s) -
Miethchen Ralf,
Hein Martin,
Reinke Helmut
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199805)1998:5<919::aid-ejoc919>3.0.co;2-3
Subject(s) - chemistry , trifluoromethyl , sugar , organic chemistry , combinatorial chemistry , alkyl
We have studied the fluoroalkylation of the glucal 1 and the galactal 4 with dibromodifluoromethane via the 2‐ C ‐bromodifluoromethyl‐substituted glycosyl bromides 2 and 5 , respectively, followed by glycosylation to the methyl β‐D‐glycosides 3 and 6 . The bromodifluoromethyl groups in the 2 position of the compounds 3 and 6 were converted into difluoromethyl and trifluoromethyl groups, respectively, giving the fluorinated monosaccharides 7 − 10 .