SYNTHESIS OF SIALIC-ACID ANALOGS WITH THE OXIME GROUP AT C-4 OR C-5 OF KDN

Authors
KAI T SUN XL TAKAYANAGI H FURUHATA K
Citation
T. Kai et al., SYNTHESIS OF SIALIC-ACID ANALOGS WITH THE OXIME GROUP AT C-4 OR C-5 OF KDN, Journal of carbohydrate chemistry, 16(4-5), 1997, pp. 521-532
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear",Biology
Journal title
Journal of carbohydrate chemistry → ACNP
ISSN journal
07328303
Volume
16
Issue
4-5
Year of publication
1997
Pages
521 - 532
Database
ISI
SICI code
0732-8303(1997)16:4-5<521:SOSAWT>2.0.ZU;2-D
Abstract
The readily available methyl (methyl 3-deoxy-5,8:7, 9-di-O-isopropylid ene-beta-D-glycero-D-galacto-2 -nonulopyranosid)onate (7) was converte d in five synthetic steps into methyl (methyl 4-acetamido-3, eoxy-beta -D-glycero-D-talo-2-nonulopyranosid)onate (11). Selective protection o f the C-4, C-7, C-8 and C-9 hydroxy groups of methyl (methyl 3-deoxy-8 , 9-O-isopropylidene-beta-D-glycero-D-galacto-2 -nonulpyranosid)onate (2) followed by oxidation of the C-5 hydroxy group and then its oximin ation gave 5-hydroxyimino derivatives(l5 and 16).