Synthese einer Kdo-haltigen pentasaccharidsequenz der inneren core- und lipid A-region von lipopolysacchariden

✍ Scribed by Hans Paulsen; Christof Krogmann

• Publisher: Elsevier Science
• Year: 1990
• Tongue: English
• Weight: 984 KB
• Volume: 205
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(90)80125-m

✦ Synopsis

Coupling of methyl (4,5,7,8-tetra-O-acetyl-3-deoxy-alpha-D-manno-2-octulopyranosyl) onate-(2----4)-methyl (5,7,8-tri-O-acetyl-3-deoxy-alpha-D-manno-octulopyranosyl bromide)onate with benzyl O-(methyl [3-deoxy-7,8,O-(tetraisopropyldisiloxan 1,3-diyl)-alpha-D-manno-octulopyranosylonate)-2-----6)-O-([( R)-3-benzyloxytetradecanoylamino]-2-deoxy-3,4-O-(tetraisopropyl disiloxan-1,3-diyl)-beta-D-glucopyranosyl)-(1----6)-3-O-benz yl- 2-[(R)-3-benzyloxytetradecanoylamino]-2-deoxy-alpha-D-glucopyranos ide gave stereo- and regio-selectively a pentasaccharide that was deprotected into alpha-Kdo-(2----4)-alpha-Kdo-(2----4)-alpha-Kdo-(2----6)-beta-D-GlcNh m-(1----6)-D-GlcNhm [Nhm = 2-deoxy-(R)-3-hydroxytetradecanoylamino].