Synthesis of 3-O-Benzoyl-1,2- O-isopropylidene-α-D-allofuranose and Its Dimesylated Derivative

Diisopropylidenated α-D-glucofuranose (1) was oxidated with CrO3-pyridine complex.Oxidated product and its hydrate were separated and were reduced together to synthesize diisopropylidenated α-D-allofuranose (3). The yield of 3 increased by 8% than that with only oxidated product as reduction substrate. Benzoylated derivative of 3 was selectively hydrolyzed and dimesylated to synthesize 3-O-benzoyl-1,2- O- isopropylidene-α-D-allofuranose (5) and its dimesylated deriva tive respectively. The overall yield of 5 from 1 was 36%. Each step and final products were anal yzed by 1H-NMR spectra and other methods. The experiments showed that the influence of acetic acid concentration on selective hydrolysis was obvious. The hydrolysis yield was 81.8%. Oxidation, reduction and other procedures were practical and had application potential.