127619-25-4Relevant academic research and scientific papers
Synthesis of Galactose-Cluster-Containing Steroid Derivatives
Peter, Martin G.,Boldt, Peter C.,Niederstein, Yvonne,Peter-Katalinic, Jasna
, p. 863 - 869 (2007/10/02)
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.
