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...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 nydrolyzed and dimesylated to synthesize 3-O-benzoyl-1 .2- O- isopropylidene-α-D-allofuranose （ 5 ） and its dimesylated derivative respectively. The overall yield of 5 from 1 was 36%. Each step and final products were analyzed 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.展开更多
基金Supported by Tianjin Natural Science Foundation ( No. 05YFJMJC09600).
文摘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 nydrolyzed and dimesylated to synthesize 3-O-benzoyl-1 .2- O- isopropylidene-α-D-allofuranose （ 5 ） and its dimesylated derivative respectively. The overall yield of 5 from 1 was 36%. Each step and final products were analyzed 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.
