Branched-chain sugars configuration determination

Chiroptical studies on 1-thio-D-glycofuranosides and 1-thio-D-glycopyranosides and a discussion of Hudson s rules [10]. Review on the chemistry and biochemistry of branched chain sugars including determination of the configuration at the branched position [11]. 

Other instances of a low hydroxyl-stretching frequency arising from the hydroxyl group (s) on a pair of 1,3-m-diaxial C—0 bonds have been reported in the spectra of methyl 2-C-methyl- 3-L-ribopyranoside (at 3512 cm. ) and methyl 3,6-anhydro-a-D-glucopyranoside (at 3500 cm. 0-The latter compound is constrained in the 1C conformation, and the band at 3512 cm. shows that the former compound is in the 1C conformation also. The occurrence of this characteristically low frequency in the spectra of some branched-chain sugars enabled their configuration to be determined by indicating the presence of such diaxial C—0 bonds. ... 

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