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Bausteine von Oligosacchariden, XXXIX. Synthese der Glycopeptide β-D-Gal(1 → 4)-α-D-GlcNAc(1 → O)-L-Ser und β-D-Gal(1 → 4)-α-D-GlcNAc(1 → O)-L-Thr

✍ Scribed by Paulsen, Hans ;Hölck, Jens-Peter

Publisher
John Wiley and Sons
Year
1982
Tongue
English
Weight
680 KB
Volume
1982
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

6‐O‐Acetyl‐2‐azido‐4‐O‐benzyl‐2‐desoxy‐3‐O‐trichloracetyl‐β‐D‐glucopyranosylchlorid (2) läßt sich in Dichlormethan/Toluol bei Gegenwart von Silbercarbonat/Silberperchlorat mit dem Serin‐derivat 3 und dem Threoninderivat 7 selektiv zu den α‐Glycosiden 5 und 9 umsetzen. In einer entsprechenden Reaktion kann das β‐Pyranosylchlorid des 2‐Azido‐2‐desoxylactose‐Derivates 12 mit 3 und 7 zu den Disaccharid‐Glycosiden 13 und 14 umgesetzt werden. Beide Reaktionen lassen sich ebenfalls stereoselektiv nur zum α‐Glycosid lenken. Durch vollständige Entblockierung von 13 und 14 sind die beiden Glycopeptide β‐D‐Gal(1 → 4)‐α‐D‐GlcNAc(1 → O)‐L‐Ser (17) und β‐D‐Gal(1 → 4)‐α‐D‐GlcNAc(1 → O)‐L‐Thr (20) zu erhalten.

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