Rp-Diastereoselective synthesis of dinucleoside methylphosphonates by the phosphoramidite approach

✍ Scribed by Peter Schell; Joachim W. Engels

• Book ID: 104260175
• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 238 KB
• Volume: 39
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(98)01972-8

✦ Synopsis

In order to obtain diastereomeric control in the azole catalyzed coupling reaction of methylphosphonamidites, 2-(2",4",6"-trimethylbiphenyl-2-yl)-4,5-dicyanoimidazole 2 was synthesized. With its use as activator Rp-diastereoselective synthesis of dinucleoside methylphosphonates could be achieved for the first time by the phosphoramidite approach. Selectivities were up to 84 / 16 (Rp / Sp). The mechanism of the reaction is based on dynamic kinetic resolution.