Stereospecific synthesis of D-erythro- and D-threo-3-C-methyl-2-deoxypentofuranosides and related nucleosides
I.I. Fedorov, Ya. E. Beztchinsky, N. A. Novikov, E. M. Kazmina, S. G. Rosenberg, S. N. Mikhailov
I. M. Sechenov 1st Medical Institute, Moscow; V. A. Engelhardt Institute of Molecular Biology, Academy of Sciences of the USSR, Moscow
Abstract: A scheme for the synthesis of 3'-C-methyl-2'-deoxynucleosides has been developed. It includes the oxydation of methyl 5-O-benzoyl-α- and β-D-erythro-pentofuranosido followed by the Grignard reaction. The obtained 3'-C-methyl-D erythro- and D-threo- derivatives after bunzoylation were transformed into l-(3'-C-methyl-2'-deoxy-p-Z)-er!//fero-pontofuranosyl)thymine and 1-(3'-C-methyl-2'-deoxy-β-D-threo-pentofuranosyl)thymine.
Russian Journal of Bioorganic Chemistry 1990, 16 (7):997-999