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

【摘要】 <正>Diisopropylidenated a-D-glucofuranose (1) was oxidated with CrO;-Pyridine complex. Oxidated product and its hydrate were separated and were reduced together to synthesize diisopro-pylidenated a-D-allofuranose (3 ). The yield of 3 increased by 8% than that with only oxidated prod-uct as reduction substrate. Benzoylated derivative of 3 was selectively hydrolyzed and dimesylated to synthesize 3-O-benzoyl-l ,2-O-isopropylidene-a-D-allofuranose (5) and its dimesylated deriva-tive respectively. The overall yield of 5 from 1 was 36%. Each step and final products were analyzed by ’H-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, re-duction and other procedures were practical and had application potential.更多还原

【Abstract】 Diisopropylidenated a-D-glucofuranose (1) was oxidated with CrO;-Pyridine complex. Oxidated product and its hydrate were separated and were reduced together to synthesize diisopro-pylidenated a-D-allofuranose (3 ). The yield of 3 increased by 8% than that with only oxidated prod-uct as reduction substrate. Benzoylated derivative of 3 was selectively hydrolyzed and dimesylated to synthesize 3-O-benzoyl-l ,2-O-isopropylidene-a-D-allofuranose (5) and its dimesylated deriva-tive respectively. The overall yield of 5 from 1 was 36%. Each step and final products were analyzed by ’H-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, re-duction and other procedures were practical and had application potential.更多还原