ASYMMETRIC-SYNTHESIS OF 4-AMINO-2,3,4-TRIDEOXYALDONIC ACIDS - NOVEL GABA C-GLYCOCONJUGATES

Authors
RASSU G PINNA L SPANU P ULGHERI F CORNIA M ZANARDI F CASIRAGHI G
Citation
G. Rassu et al., ASYMMETRIC-SYNTHESIS OF 4-AMINO-2,3,4-TRIDEOXYALDONIC ACIDS - NOVEL GABA C-GLYCOCONJUGATES, Tetrahedron, 49(29), 1993, pp. 6489-6496
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
29
Year of publication
1993
Pages
6489 - 6496
Database
ISI
SICI code
0040-4020(1993)49:29<6489:AO4A-N>2.0.ZU;2-2
Abstract
Stereochemically defined 4-amino-2,3,4-trideoxyaldonic acids 4, repres entatives of a new progeny of C-glycosylated GABAs, have been synthesi zed from the readily available aldehydo precursors 1 in three steps an d 60-75% overall yields. The key reaction is the SnCl4-assisted regio- and diastereoselective homologation of 1 with the nitrogen-containing five-membered ring siloxydiene TBSOP.