Reduction of 1,6:2,5-dianhydro-3,4-di-O-methanesulfonyl-1-thio-D- glucitol with LAH afforded the corresponding 3,4-dihydroxy compound in a yield of 51% and six by-products were isolated after acetylation. Three differed from the original molecule only in the substituents, which were AcO at C-3 and H, CH3S and CH3SCH2S at C-4, respectively. The other compounds had a rearranged skeleton and were 1,4:2,5-dianhydro-1-thio-D-galactitol derivatives, containing the AcO group at C-3 and the aforementioned three substituents attached to C-6. A mechanism is suggested for the rearrangement, and for the formation of the substituents including the fate of the methanesulfonyloxy groups on reduction with LAH which is generally applicable to any mesyloxy derivative.
- Sulfonic acids and derivatives
ASJC Scopus subject areas
- Drug Discovery
- Organic Chemistry