Kelvin K. Olgivie, D. Entwistle
Mar 2, 1981
Citations
0
Influential Citations
33
Citations
Journal
Carbohydrate Research
Abstract
Abstract The tert -butyldimethylsilyl group undergoes isomerization between 0-2′ and 0-3′ in ribonucleosides in solution. Isomerization is most rapid in protic solvents and extremely slow in such solvents as dry dimethyl sulfoxide, pyridine, oxolane, chloroform, or N , N -dimethylformamide. Isomerization is much faster for uridine and adenosine derivatives than for cytidine and guanosine derivatives. With N -benzoyl-nucleosides, an unusual debenzoylation of 2′- and/or 5′-silylated nucleosides occurs in methanol; it is fastest in N -benzoyleytidine and N -benzoyladenosine and much slower in N -benzoylguanosine. The isomerization and debenzoylation studies were monitored by 1.c., and separation of the isomeric, silytated nucleosides by 1.c. is described.