A NEW AND CONCISE SYNTHESIS OF 3-DEOXY-D-ARABINO-2-HEPTULOPYRANOSONICACID (DAH) AND DERIVATIVES THROUGH THE RADICAL CHEMISTRY OF BARTON ESTERS

Authors
BARTON DHR LIU WS
Citation
Dhr. Barton et Ws. Liu, A NEW AND CONCISE SYNTHESIS OF 3-DEOXY-D-ARABINO-2-HEPTULOPYRANOSONICACID (DAH) AND DERIVATIVES THROUGH THE RADICAL CHEMISTRY OF BARTON ESTERS, Tetrahedron letters, 38(3), 1997, pp. 367-370
Citations number
26
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
3
Year of publication
1997
Pages
367 - 370
Database
ISI
SICI code
0040-4039(1997)38:3<367:ANACSO>2.0.ZU;2-X
Abstract
Barton ester-based radical chemistry was applied in the synthesis of 3 -deoxy-D-orobino-2-heptulopyranosonic acid (DAH) from commercial D-rib onolactone, The radical reaction with olefin 2, followed by aqueous wo rk-up, provided the seven-carbon sugar compounds 5 and 6 (3:1) in 60% yield. Removal of the isopropylidene groups from 5 and hydrolysis of t he ethyl ester yielded the DAH barium salt quantitatively. Copyright ( C) 1996 Elsevier Science Ltd