Sucrose → 6'-Chloro-6'-deoxysucrose

Participants

Reaction Steps

Attempts to synthesize cyclic sulfates of unprotected sugars with sulfuryl chloride and pyridine have been reported. Bragg P. D. et al, Can. J. Chem. 1959, 37, 1412. However, this reaction is not clean, and several side products are isolated. For example, reaction of sucrose with sulfuryl chloride at -78° C. afforded the 6,6'-dichloro-6,6'-deoxysucrose and 6'-chloro-6'-deoxysucrose in 43 and 29% yields, respectively. At room temperature, a complex mixture was formed from which 3',4'-anhydro-1',6'-dichloro-1',6'-dideoxy-β-D-ribo-hexulofuranoside. 2,3-cyclic sulfate was isolated in 17% yield, showing that chlorination occurred as well as inversion of configuration during cyclic sulfate formation. Ballard J. M, et al., J. Chem. Soc., Perkin Trans. 1, (1973) 1524-1528.

Provenance & Evidence