250710-45-3Relevant academic research and scientific papers
Synthesis of sulfur-containing analogues of αGalNAc (Tn-antigen) and βGal1,3αGalNAc (T-antigen)
Wenzl, Irmgard,Neuwirth, Norbert,Hedenetz, Alexander G.,Fiedler, Christian,Streicher, Hansjoerg,Unger, Frank M.,Schmid, Walther
, p. 531 - 540 (2007/10/03)
A method for the preparation of thio-analogues of the T- and Tn-antigen was developed. Thus, starting from a known N-acetamido-glucoside derivative, the epidithio analogue of the Tn-antigen was accessible in a four-step reaction sequence. The corresponding epidithio analogue and the thioanhydro derivative of the T-antigen were synthesized starting from a disaccharide derivative. For the preparation of the epidithio analogue the sulfur atoms were introduced via thiocyanates in a stepwise fashion, using mesylate as the leaving group at C-6 and triflate as the leaving group at C-4 in the reducing carbohydrate moiety. The synthesis of the thioanhydro analogue was achieved by introducing a thiocyanate group at C-6 into the glucose moiety, followed by subsequent displacement of a mesylate group at C-4 under inversion of configuration utilizing sodium methoxide.
A Novel approach to β-(1-→4)-linked thiodisaccharides starting from disulfide sugars
Wenzl, Irmgard,Kaehlig, Hanspeter,Unger, Frank M.,Schmid, Walther
, p. 1137 - 1145 (2007/10/03)
Glycosylation of monosaccharides 4, 8, and 10 containing an intramolecular disulfide bridge by applying Helferich-conditions and an excess of acctobromohexose 5 or 11 as donor substrate yielded 6-thiocyanato-β-(1-→4)-thiodisaccharides 6, 9, and 12 regio-and stereospecifically in moderate to good yields. In addition, the formation of trisaccharides 7 and 13 could be observed, albeit in low yield. This novel route for thioglycoside formation may open access to a variety of bioactive disaccharide analogues.
