Synthesis of Protected 4-Amino- and 4-Azido-3-hydroxy-l-prolines from d-Glucose

Abstract

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-α-d-glucofuranose, which was subjected to mesylation of the 5- and 6-hydroxy groups and subsequent intramolecular S_N2 displacement of the 6-O-mesyl group by the 3-(benzyloxycarbonyl)amino group to give a pyrrolidine ring. The resulting intermediate underwent intermolecular S_N2 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.

Key words

amino acids - chemoselectivity - carbohydrates - cyclization - pyrroles - stereoselective synthesis

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