IMPROVED STEREOSELECTIVE SYNTHESIS OF BOTH METHYL ALPHA-GLYCOSIDES AND BETA-GLYCOSIDES CORRESPONDING TO THE AMINO SUGAR COMPONENT OF THE E-RING OF CALICHEAMICIN (I)(GAMMA-1) AND ESPERAMICIN A(1)

Authors
BADALASSI F CROTTI P FAVERO L MACCHIA F PINESCHI M
Citation
F. Badalassi et al., IMPROVED STEREOSELECTIVE SYNTHESIS OF BOTH METHYL ALPHA-GLYCOSIDES AND BETA-GLYCOSIDES CORRESPONDING TO THE AMINO SUGAR COMPONENT OF THE E-RING OF CALICHEAMICIN (I)(GAMMA-1) AND ESPERAMICIN A(1), Tetrahedron, 53(42), 1997, pp. 14369-14380
Citations number
30
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
42
Year of publication
1997
Pages
14369 - 14380
Database
ISI
SICI code
0040-4020(1997)53:42<14369:ISSOBM>2.0.ZU;2-L
Abstract
The monosaccharide component (alpha and beta-anomer) of the E Ring of calicheamicin (I)(gamma 1) and esperamicin A(1) has been synthetized b y an efficient and improved stereoselective procedure starting from me thyl 2-deoxy-alpha- and beta-D-ribopyranoside. The synthetic procedure makes use, in each case, of a cyclic sulphate and of the regioselecti ve ring opening of an intermediate activated aziridine. (C) 1997 Elsev ier Science Ltd.