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Synthesis of 3′-deoxyadenosine-3′-spirocyclopropane, 3′-deoxy-uridine-3′-spirocyclopropane, and 5′-deoxy-4′,5′-methanoadenosine

✍ Scribed by Vicente Samano; Morris J. Robins

Publisher
Elsevier Science
Year
1994
Tongue
French
Weight
268 KB
Volume
35
Category
Article
ISSN
0040-4039

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✦ Synopsis

Cycloaddition of diazomethane with 3'-deoxy-3'-methylene-and 4',S-didehydro-5'-deoxynucleoside derivative8 followed by sensitized photochemical extrusion of nitrogen provided the previously unreported 3'-and 4'-spirocyclopropane nucleoside derivatives. Enhancement of the cycloaddition reactions by electron withdrawing benzoyl protecting group8 was observed.

The development of AZT. DDI, and DDC as therapeutic agents for the treatment of AIDS has stimulated research on structurally novel nucleoside analogues with a variety of biological activities.2 Examples of newer sugar-modified nucleoside analogues arc 2',3'-dideoxy-2',3'-a-methanocytidine (A)3 and TSAO (ILQ4

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