Stereoselective Syntheses of α-D-Ribopyranosyl Disaccharides [1]
2014
Dahlhoff, Wilhelm V. | Schroth, Gerhard | Gabor, Barbara
1 → 6-, 1 → 3- and 1 → 1-linked α-D-ribopyranosyl disaccharides 2a, 2b, and 5, respectively are prepared with ≥95% stereoselectivities by reacting 3-O-acetyl-2,4-O-phenylboranediylβ-D-ribopyranosyl bromide (1) with the sodium organooxytriethylborates of 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose, 1,2 : 5,6-di-O-isopropylidene-α-D-glucofuranose and with hexabutyl-distannoxane, respectively. After deboronation and deacetylation 3a, 3b, and 6 are obtained and these are acetylated to give 4a, 4b, and 7.
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