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- W2322986481 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 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 S N 2 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." @default.
- W2322986481 created "2016-06-24" @default.
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- W2322986481 date "2012-07-27" @default.
- W2322986481 modified "2023-10-04" @default.
- W2322986481 title "Synthesis of Protected 4-Amino- and 4-Azido-3-hydroxy-l-prolines from d-Glucose" @default.
- W2322986481 doi "https://doi.org/10.1055/s-0032-1316612" @default.
- W2322986481 hasPublicationYear "2012" @default.
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