Synlett 2007(20): 3149-3154  
DOI: 10.1055/s-2007-1000822
LETTER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Enantiomerically Pure 4-Substituted Riboses

Adrian Maddaforda, Thierry Guyota, David Leesea, Rebecca Glena, James Harta, Xiurong Zhanga, Ray Fishera, Donald S. Middletonb, Cheryl L. Dohertyc, Nick N. Smithb, David C. Pryde*b, Scott C. Suttond
a Peakdale Molecular Ltd., Peakdale Science Park, Sheffield Road, Chapel-en-le-Frith, High Peak, SK23 0PG, UK
b Discovery Chemistry, Pfizer Global Research and Development, Ramsgate Road, Sandwich, CT13 9NJ, UK
e-Mail: David.Pryde@pfizer.com;
c Material Sciences, Pfizer Global Research and Development, Ramsgate Road, Sandwich, CT13 9NJ, UK
d Lead Discovery, Pfizer Global Research and Development, 10777 Science Centre Drive, San Diego, CA 92121, USA
Weitere Informationen

Publikationsverlauf

Received 5 October 2007
Publikationsdatum:
03. Dezember 2007 (online)

Zoom Image

Abstract

An efficient and flexible synthesis of 4-substituted ribose analogues is described. The key step involves the simple addition of a Grignard reagent to a ketone derived from a commercially available ribose. The addition of a range of Grignard reagents proceeded in high yield and with complete stereocontrol, to provide a single enantiomer in every case, the identity of which was confirmed by single-crystal X-ray crystallography. This addition is unaffected by substitution at the 2-position of the starting ribose.