Efficient syntheses of 1-S-alkyl-1-thio-L-ribitols, D-lyxitols and L-xylitols from D-pentono-1,4-lactones

Authors
Lalot, J Manier, G Stasik, I Demailly, G Beaupere, D
Citation
J. Lalot et al., Efficient syntheses of 1-S-alkyl-1-thio-L-ribitols, D-lyxitols and L-xylitols from D-pentono-1,4-lactones, CARBOHY RES, 335(1), 2001, pp. 55-61
Citations number
17
Categorie Soggetti
Agricultural Chemistry","Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
CARBOHYDRATE RESEARCH
ISSN journal
00086215 → ACNP
Volume
335
Issue
1
Year of publication
2001
Pages
55 - 61
Database
ISI
SICI code
0008-6215(20010921)335:1<55:ESO1DA>2.0.ZU;2-D
Abstract
The thioalkylation of unprotected 5-bromo-5-deoxy-D-ribono, D-arabinono, an d D-xylono-1,4-lactone was performed with the alkylthiol-sodium hydride rea gent. The corresponding 5-S-alkyl-5-thio-D-pentono-1,4-lactones were isolat ed in good yields (82-95%). Reduction with NaBH4 of these derivatives gave the 1-S-alkyl-1-thio-L-ribitols, D-lyxitols and L-xylitols in 85-96% yields . (C) 2001 Elsevier Science Ltd. All rights reserved.