beta-fragmentation of anomeric alkoxy radicals from 1,3,4,5-tetra-O-benzyl-hex-2-ulopyranoses: a simple synthesis of new aldehydo tetrose building blocks

Authors
Adinolfi, M Barone, G Iadonisi, A
Citation
M. Adinolfi et al., beta-fragmentation of anomeric alkoxy radicals from 1,3,4,5-tetra-O-benzyl-hex-2-ulopyranoses: a simple synthesis of new aldehydo tetrose building blocks, SYNLETT, (1), 1999, pp. 65-66
Citations number
15
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
1
Year of publication
1999
Pages
65 - 66
Database
ISI
SICI code
0936-5214(199901):1<65:BOAARF>2.0.ZU;2-4
Abstract
1,3,4,5-Tetra-O-benzyl-hex-2-ulopyranoses can be easily converted into 2,3- di-O-benzyl-4-O-benzyloxyacetyl-tetroses. The procedure exploits the recent ly introduced conversion of aldohexoses to 2-ketohexoses by Meerwein-Ponndo rf-Verley/Oppenauer reaction induced by Sm(III) species to obtain sugar hem iketals to be used as substrates for a Suarez reaction.