NUCLEIC-ACID RELATED-COMPOUNDS .58. PERIODINANE OXIDATION, SELECTIVE PRIMARY DEPROTECTION, AND REMARKABLY STEREOSELECTIVE REDUCTION OF TERT-BUTYLDIMETHYLSILYL-PROTECTED RIBONUCLEOSIDES - SYNTHESIS OF 9-(BETA-D-XYLOFURANOSYL)ADENINE OR 3'-DEUTERIOADENOSINE FROM ADENOSINE

: Treatment of 9-(2,5-bis-o-(tert-butyldi-methylsilyl)-,β-D-eryt/erythro-pentofuran-3-ulosyl)adenine (2) with sodium triacetoxyborohydride in acetic acid and de-protection gave adenosine (lb) and 9-(β-D-xylo-furanosyl)adenine (3) [3:97 (1:32)]. Selective 05’ deprotection of 2, and hydroxyl-directed reduction with the hydride (or deuteride) reagent gave lb (or 3’-deuterio, lc) and 3 [99.5:0.5 (199:1)] after deprotection. © 1990, American Chemical Society. All rights reserved.