Variable strategy toward carbasugars and relatives. 2. Diversity-based synthesis of beta-D-xylo, beta-D-ribo, beta-L-arabino, and beta-L-lyxo 4a-carbafuranoses and (4a-carbafuranosyl)thiols

G Rassu; L Auzzas; L Pinna; V Zambrano; L Battistini; F Zanardi; L Marzocchi; D Acquotti; G Casiraghi

doi:10.1021/jo010585v

Variable strategy toward carbasugars and relatives. 2. Diversity-based synthesis of beta-D-xylo, beta-D-ribo, beta-L-arabino, and beta-L-lyxo 4a-carbafuranoses and (4a-carbafuranosyl)thiols

J Org Chem. 2001 Nov 30;66(24):8070-5. doi: 10.1021/jo010585v.

Authors

G Rassu¹, L Auzzas, L Pinna, V Zambrano, L Battistini, F Zanardi, L Marzocchi, D Acquotti, G Casiraghi

Affiliation

¹ Istituto per l'Applicazione delle Tecniche Chimiche Avanzate ai Problemi Agrobiologici del CNR, I-07100 Sassari, Italy.

PMID: 11722207
DOI: 10.1021/jo010585v

Abstract

The silyloxy diene-based construction of carbasugars, previously exploited for the synthesis of four carbocyclic furanose and pyranose analogues, has been investigated further. By introducing a novel silylative cycloaldolization protocol and by adjusting a couple of minor transformations, the efficiency of this synthetic sequence was greatly improved. Through a series of lactone/thiolactone aldehyde cyclization precursors, four carbafuranoses (4a-carba-beta-D-xylofuranose, 4a-carba-beta-D-ribofuranose, 4a-carba-beta-L-arabinofuranose, and 4a-carba-beta-L-lyxofuranose) and four (carbafuranosyl)thiols [(4a-carba-beta-D-xylofuranosyl)thiol, (4a-carba-beta-D-ribofuranosyl)thiol, (4a-carba-beta-L-arabinofuranosyl)thiol, and (4a-carba-beta-L-lyxofuranosyl)thiol] were assembled. From this study, it was shown that these constructions tolerate a variety of precursors, and in many instances, they are suitable for scaling-up.