Carbohydrate research

Synthesis of 3-amino-2, 3, 6-trideoxy-2-fluoro-l-talose and-d-allose [(R)-2-fluoro-l-daunosamine and (R)-2-fluoro-d-ristosamine]

HH Baer, FH Mateo, L Siemsen

Index: Baer; Hernandez Mateo; Siemsen Carbohydrate research, 1990 , vol. 195, # 2 p. 225 - 245

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Citation Number: 12

Abstract

Abstract The title compounds were synthesized (as methyl glycosides) starting from 1, 3, 4, 6- tetra-O-acetyl-2-deoxy-2-fluoro-β-d-glycopyranose. Stereoselective methods of glycosylation gave, via the tri-O-acetylglycopyranosyl bromide, the methyl 2-deoxy-2-fluoro-α-and-β-d- glycopyranoside triacetates. Each anomer was O-deacetylated and further transformed into the corresponding, 4, 6-O-benzylidenated 3-triflate, and the triflates were converted by ...