A new procedure for the synthesis of azasugars

Luigi Lay, Francesco Nicotra, Angelo Paganini, Cristina Pangrazio, Luigi Panza

Research output: Contribution to journalArticlepeer-review

Abstract

Reaction of the commercially available 2,3,5-tri-O-benzyl-D-arabinose with a primary amine (RNH2) affords the arabinofuranosylamine 2, which on treatment with a Grignard reagent stereoselectively gives the aminoalcohol 3. 3 is an useful precursor of azasugars: it is converted into the pyrrolidine 4 by treatment with Tf2O-Py, whereas by oxidation with PCC it affords the lactam 5 which can be reduced to the corresponding amine 6.

Original languageEnglish
Pages (from-to)4555-4558
Number of pages4
JournalTetrahedron Letters
Volume34
Issue number28
DOIs
Publication statusPublished - 9 Jul 1993
Externally publishedYes

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