Synthesis of Derivatives of 2,6-Dideoxy-2,2-Difluoro-3-O-Methyl-l-Arabinopyranose (2,2-Difluorooleandrose)
- 1 March 1989
- journal article
- research article
- Published by Taylor & Francis in Journal of Carbohydrate Chemistry
- Vol. 8 (1), 103-113
- https://doi.org/10.1080/07328308908047995
Abstract
L-Oleandrose is the carbohydrate constituent of the potent anthelmintic agents the avermectins. Diethylaminosulfur tri-fluoride treatment of appropriate uloses did not give gem-difluoro sugars. Trifluorofluoroxymethane or xenon difluoride addition to the double bond of 4-O-benzoyl-6-deoxy-2-fluoro-3-O-methyl-L-glucal produced protected 2,2-difluorooleandrose derivatives activated at their anomeric center and ready for glycosidation.This publication has 3 references indexed in Scilit:
- Synthesis of C-2″β- and C-2″α-fluoro avermectin B1aJournal of the Chemical Society, Chemical Communications, 1987
- Synthesis ofTetrahedron Letters, 1977
- Steric and electrostatic interactions in reactions of carbohydrates. III. Direct displacment of the C-2 sulfonate of methyl 4,6-O-benzylidene-3-O-methyl-2-O-methylsulfonyl-.beta.-D-gluco- and -mannopyranosidesThe Journal of Organic Chemistry, 1974