TY  - GEN
A1  - Peter, Martin G.
A1  - Boldt, Peter C.
A1  - Niederstein, Yvonne
A1  - Peter-Katalinić, Jasna
T1  - Synthesen von Galactose-Cluster-haltigen Steroid-Derivaten
N2  - 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.
T3  - Zweitveröffentlichungen der Universität Potsdam : Mathematisch-Naturwissenschaftliche Reihe - paper 042 
KW  - Glycoconjugates
KW  - Galactosides
KW  - Steroid esters
KW  - Amphiphiles
KW  - Glycopeptides
Y1  - 2008
UR  - https://publishup.uni-potsdam.de/frontdoor/index/index/docId/1545
UR  - https://nbn-resolving.org/urn:nbn:de:kobv:517-opus-16783
ER  -