Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1390540 | Carbohydrate Research | 2011 | 6 Pages |
Abstract
Per-O-tert-butyldimethylsilyl-α,β-d-galactofuranosyl isothiocyanate (4) was synthesized by the reaction of per-O-TBS-β-d-galactofuranose (1) with KSCN, promoted by TMSI. Upon O-desilylation (1,2-dideoxy-α-d-galactofuranoso)[1,2d]-1,3-oxazolidine-2-thione (6), the cis-fused bicyclic thiocarbamate was obtained as the only product. Conformational analysis, aided by molecular modelling, showed two stable twist forms (3T4 and 4TO) for the five-membered sugar ring in 6. In aqueous solution, the equilibrium favours the first conformation (3:1 ratio). On the other hand, this ratio decreases for less polar solvents.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Luciana Baldoni, Carlos A. Stortz, Carla Marino,