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. LayPrimo
;
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.
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