期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 66, 期 14, 页码 4878-4886出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo010299j
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The [3.2.0]bicyclic beta -nucleoside analogue 5 has been designed as a conformationally restricted analogue of the anti-HIV drug AZT. The synthesis of 5 as well as its a-anomer 29 is hereby described. The synthesis was accomplished from D-arabinose via a modified Corey-Link procedure stereoselectively incorporating the azide moiety as well as a methyl ester function. When the tert-butyldiphenylsilyl group was used as a permanent protecting group, a selective formation of an oxetane ring failed. When using the p-methoxyphenyl group as a permanent protecting group, 5 and 29 were efficiently obtained via a selective reduction of the ester, a nucleobase coupling followed by separation of the anomers and ring-closing procedures. The nucleoside 5 is conformationally restricted in an unusual O4 ' -endo (East) conformation, which is an intermediate between the North-and South-type conformations. Nevertheless, neither 5 nor 29 displayed any anti-HIV activity.
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