TY - JOUR
T1 - Synthesis of 3-deoxy-3-nucleobase-2,5-anhydro-D-mannitol
T2 - A novel class of hydroxymethyl-branched isonucleosides
AU - Lei, Z.
AU - Min, J. M.
AU - Zhang, L. H.
N1 - Funding Information:
This work was supported by the National Natural Science Foundation of China and by a grant (G 1998051103) from the Ministry of Science and Technology of China.
PY - 2000/7/28
Y1 - 2000/7/28
N2 - 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. (C) 2000 Elsevier Science Ltd.
AB - 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. (C) 2000 Elsevier Science Ltd.
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U2 - 10.1016/S0957-4166(00)00246-9
DO - 10.1016/S0957-4166(00)00246-9
M3 - Article
AN - SCOPUS:0034725619
SN - 0957-4166
VL - 11
SP - 2899
EP - 2906
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 14
ER -