Synthesis of 3-deoxy-3-nucleobase-2,5-anhydro- d-mannitol: a novel class of hydroxymethyl-branched isonucleosides

A concise synthesis of 3-deoxy-3-nucleobase-2,5-anhydro- d-mannitol 6( a– d) has been achieved, using the deamination of 2-amino-2-deoxy- d-glucose to construct in one step the sugar skeleton with the desired sense of chirality at each asymmetric center. The selective dibenzoylation of 2,5-anhydro-...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2000-07, Vol.11 (14), p.2899-2906
Main Authors: Lei, Z, Min, J.M, Zhang, L.H
Format: Article
Language:English
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Summary:A concise synthesis of 3-deoxy-3-nucleobase-2,5-anhydro- d-mannitol 6( a– d) has been achieved, using the deamination of 2-amino-2-deoxy- d-glucose to construct in one step the sugar skeleton with the desired sense of chirality at each asymmetric center. The selective dibenzoylation of 2,5-anhydro- d-mannitol 9 was investigated, and the key epoxide intermediate 13 was obtained in good yield via an intramolecular Mitsunobu reaction. The process of opening of epoxide 13 by nucleobases appeared to be regioselective.
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(00)00246-9