A General Method for the Synthesis of 2′-O-Modified Ribonucleosides

✍ Scribed by Thomas H. Keller; Robert Häner

• Publisher: John Wiley and Sons
• Year: 1993
• Tongue: German
• Weight: 635 KB
• Volume: 76
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19930760212

✦ Synopsis

Abstract

A general way for the functionalization of ribonucleosides is described. The method involves the synthesis of the methyl‐ribofuranoside derivative 6 equipped with a linker at the 2‐hydroxy group (Scheme 2). After introduction of the nucleic‐acid bases under standard conditions (Scheme 3), the resulting β‐D‐ribonucleosides 8 and 10 are further transformed to derivatives with lipophilic, intercalating, and aminoalkyl residues at the linker moiety. In this way, 2′‐modified 5‐methyluridines 12, adenosines 13, and 5‐methylcytidines 15 and 16 were prepared (Scheme 4).