New synthetic routes to protected purine 2'-O-methylriboside-3'-O-phosphoramidites using a novel alkylation procedure

• Published in: Nucleic acids research Vol. 18; no. 1; pp. 41 - 49
• Main Authors: SPROAT, B. S, BEIEJER, B, IRIBARREN, A
• Format: Journal Article
• Language: English
• Published: Oxford Oxford University Press 11-01-1990
• Subjects: Adenine Nucleotides; Analytical, structural and metabolic biochemistry; Biological and medical sciences; Chemical Phenomena; Chemistry; Fundamental and applied biological sciences. Psychology; Guanine Nucleotides; Inosine Nucleotides; Methylation; Nucleic acids; Nucleic bases, nucleotides; Oligoribonucleotides - chemical synthesis; Organophosphorus Compounds; Chemical modification; Purine; Method; Chemical synthesis; Protection; Alkylation
• ISSN: 0305-1048; 1362-4962
• DOI: 10.1093/nar/18.1.41

A highly selective alkylation procedure has been developed enabling new synthetic routes to be established for protected purine 2'-O-methylriboside-3'-O-phosphoramidites; building blocks for the assembly of 2'-O-methyloligoribonucleotides. The new procedure avoids the use of the highly toxic and potentially explosive reagent diazomethane and is far superior to the use of silver oxide/methyl iodide. Moreover, the use of highly versatile key intermediates will enable the synthesis of a wide variety of base modified analogues as well as other 2'-O-alkylriboside derivatives.