Synthesen von Galactose-Cluster-haltigen Steroid-Derivaten

  • The synthesis of galactose clusters that are linked to a steroid moiety by a peptide-like spacer unit is described. The galactose cluster is obtained by Koenigs-Knorr glycosylation of TRIS-Gly-Fmoc (2b) under Helferich conditions. Peptide and ester bonds are formed after activation of carboxylic acids as diphenylthiophene dioxide (TDO) esters. 6a is synthesized in a convergent way by coupling of (Ac4Gal)3-TRIS-Gly (3e) with cholesteryl TDO succinate (5b). Coupling of (Ac4Gal)3-TRIS-Gly hydrogen succinate (3f) with Gly-O-Chol (5d) by means of EEDQ yields 6d. Reaction of (Ac4Gal)3-TRIS-Gly-SUCC-O-TDO (3g) with 25-hydroxycholesterol leads in a linear sequence to the oxysterol derivative 6f. Selective cleavage of the acetyl groups from galactose units yields the known compound 6b and the new derivatives 6e and 6g.

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Metadaten
Author:Martin G. Peter, Peter C. Boldt, Yvonne Niederstein, Jasna Peter-Katalinić
URN:urn:nbn:de:kobv:517-opus-16783
Series (Serial Number):Postprints der Universität Potsdam : Mathematisch-Naturwissenschaftliche Reihe (paper 042)
Document Type:Postprint
Language:German
Date of Publication (online):2008/03/14
Year of Completion:1990
Publishing Institution:Universität Potsdam
Release Date:2008/03/14
Tag:Amphiphiles; Galactosides; Glycoconjugates; Glycopeptides; Steroid esters
Source:Liebigs Annalen der Chemie, 9 (1990) , S. 863-869 - ISSN 1099-0690; 0170-2041
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Extern / Extern
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Licence (German):License LogoKeine Nutzungslizenz vergeben - es gilt das deutsche Urheberrecht
Notes extern:
first published in:
Liebigs Annalen der Chemie - 9 (1990), S. 863 - 869
ISSN: 1434-193X (print), 1099-0690 (online)
doi: 10.1002/jlac.1990199001162