A synthetic route to 3-C-alkyl (or 3-C-phenyl-) 2,3-dideoxy-D-erythro-pentono-1,4-lactones: intermediates in the synthesis of 2(3H)-furanones

• Published in: Carbohydrate research Vol. 253; p. 207
• Main Authors: Raveendranath, P C, Blazis, V J, Agyei-Aye, K, Hebbler, A K, Gentile, L N, Hawkins, E S, Johnson, S C, Baker, D C
• Format: Journal Article
• Language: English
• Published: Netherlands 03-02-1994
• Subjects: 4-Butyrolactone - analogs & derivatives; 4-Butyrolactone - chemical synthesis; 4-Butyrolactone - chemistry; Anti-Bacterial Agents - chemical synthesis; Carbohydrate Conformation; Furans - chemical synthesis; Furans - chemistry; Indicators and Reagents; Lactones - chemical synthesis; Magnetic Resonance Spectroscopy; Nucleosides - chemical synthesis; Optical Rotation; Ribose - analogs & derivatives
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(94)80066-9

A series of 3-C-alkyl- (and 3-C-phenyl-) 2,3-dideoxy-D-erythro-pentono-1,4-lactones, compounds which are important in the synthesis of modified nucleosides and antibiotic sugars, were synthesized from D-ribonolactone. By a route that proceeded via 5-O-protected D-ribonolactone, 5-O-protected 2,3-dideoxy-D-glycero-pent-2-enono-1,4-lactones were synthesized and reacted with R2CuLi or a complex PhSCu(RMgBr)n to give respectively the 3-C-alkyl or 3-C-phenyl compounds. Details of the preparation of the O-protected intermediates, as well as the selection of the organometallic reagents, are provided.