Nucleosides and Nucleotides. 139. Stereoselective Synthesis of (2′S)-2′-C-Alkyl-2′-deoxyuridines

Abstract

A synthetic method for (2′S)-2′-C-alkyl-2′-deoxyuridines (9) has been described. Catalytic hydrogenation of 1-[2-C-alkynyl-2-O-methoxalyl-3,5-O-TIPDS-β-D-arabino-pentofuranosyl]uracils (5) gave 1-[2-C-(2-alkyl)-2-O-methoxalyl-3,5-O-TIPDS-β-D-arabino-pentofuranosyl]uracils (4) as a major product, which were then subjected to the radical deoxygenation, affording (2′S)-2′-alkyl-2′-deoxy-3′,5′-O-TIPDS-uridines (7) along with a small amount of their 2′R epimers.

(1) Part 138: Minakawa, N.; Kojima, N.; Matsuda, A. Heterocycles in press.

^#This paper is dedicated to Dr. Yoshihisa Mizuno on the occasion of his 75th birthday.

Notes

(1) Part 138: Minakawa, N.; Kojima, N.; Matsuda, A. Heterocycles in press.

^#This paper is dedicated to Dr. Yoshihisa Mizuno on the occasion of his 75th birthday.