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[摘要]：Differentially protected 4-azido- or 4-amino-3-hydroxy-L-prolines were synthesized in good overall yields (21-31%) from D-glucose. The synthetic strategy involved conversion of D-glucose into 3-[(benzyloxycarbonyl)amino]-3-deoxy-1,2-O-isopropylidene-alpha-D-glucofuranose, which was subjected to mesylation of the 5- and 6-hydroxy groups and subsequent intramolecular S(N)2 displacement of the 6-O-mesyl group by the 3-(benzyloxycarbonyl) amino group to give a pyrrolidine ring. The resulting intermediate underwent intermolecular SN2 displacement of the 5-O-mesyl group with sodium azide, hydrolysis of 1,2-acetonide group, treatment with sodium periodate, and Pinnick oxidation to give the required compounds. |
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