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.

A NEW PROCEDURE FOR THE SYNTHESIS OF AZASUGARS / L. Lay, F. Nicotra, A. Paganini, C. Pangrazio, L. Panza. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 34:28(1993), pp. 4555-4558. [10.1016/0040-4039(93)88084-V]

A NEW PROCEDURE FOR THE SYNTHESIS OF AZASUGARS

L. Lay
Primo
;
1993

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.
Settore CHIM/06 - Chimica Organica
1993
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/186269
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