Selective protection of hydroxyl groups in deoxynucleosides using alkylsilyl reagents.

✍ Scribed by Kelvin K. Ogilvie; Elaine A. Thompson; Michael A. Quilliam; John B. Westmore

• Publisher: Elsevier Science
• Year: 1974
• Tongue: French
• Weight: 157 KB
• Volume: 15
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)91764-2

✦ Synopsis

The chemical synthesis of oligonucleotides requires the availability of versatile reagents for protecting the hydroxyl and amino groups of nucleosides. We have recently described (1) the tert-butyldimethylsilyl (TBDNS) group as an exceedingly useful group for protecting the hydroxyl functions of nucleosides. This report describes a series of silyl groups which (a) provide a range of selectivity toward the 5'-hydroxyl group in deoxynucleosides; (b) provide a range of stabilities toward acid and base hydrolysis and which (c) all show different rates of acid hydrolysis for 5'versus 3' substitution. This allows perhaps for the first time a rapid and 80 Ttl