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A new procedure for the preparation of 3′-o-alkyl derivatives of 2′-deoxyribonucleosides

✍ Scribed by Bhalchandra V. Joshi; Colin B. Reese

Publisher
Elsevier Science
Year
1990
Tongue
French
Weight
113 KB
Volume
31
Category
Article
ISSN
0040-4039

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✦ Synopsis

2'-Deoxy-2'-mercaptouridine (7) has been converted, via its 2'-5 3'-oalkylidine derivatives (g), into the corresponding 3'-G-alkyl-2'-deoxyuridfnea (2).

2',3'-Dideoxynucleosides [e.g. 2',3'-dideoxycytidine (1) and 2',3'-dideoxyinosine (z)] and 2',3'-dideoxynucleoside derivatives with 3'substituents other than OH [e.g. 3'-

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The presence of cesium carbonate and tetrabutylammonium iodide (TBAI) facilitated efficient O-alkylation of alcohols with alkyl halides, giving rise to the exclusive formation of mixed alkyl carbonates, The cesium effect was also examined comparatively with other alkali carbonates.