Preparation of S-glycoside surfactants and cysteine thioglycosides using minimally competent Lewis acid catalysis

Carbohydrate Research
Lajos Z SzabòRobin Polt

Abstract

Here we report a method for the preparation of anomerically pure β-S-glycopyranosides (1,2-trans-glycosides) from the corresponding peracetate donors. S-glycosylation was performed in CHCl3 at reflux in the presence of a catalytic amount of InBr3. Deacylation of the intermediate peracetates were achieved under Zemplén conditions. Five pyranose examples, monosaccharides D-glucose and D-galactose and disaccharides cellobiose, maltose, and lactose, were used as donors, and five thiols including an α/ω dithiol and Fmoc-L-cysteine were used as acceptors. Melting points, high res MS, [α]D and NMR data ((1)H and (13)C, including COSY, HSQC and HMBC) are reported for compounds not previously described.

References

Dec 25, 1996·Journal of Colloid and Interface Science·C MoustyD Plusquellec
Jul 15, 1998·The Journal of Membrane Biology·D A Brown, E London
Nov 17, 2004·Langmuir : the ACS Journal of Surfaces and Colloids·Atte J KumpulainenJan Christer Eriksson
Aug 16, 2005·Chemical Society Reviews·Jeroen D C CodéeGijsbert A van der Marel
Dec 8, 2005·Journal of the American Chemical Society·Matthew S MacauleyDavid J Vocadlo
Jan 29, 2009·Angewandte Chemie·Xiangming Zhu, Richard R Schmidt
Oct 1, 2011·Journal of Peptide Science : an Official Publication of the European Peptide Society·Hidekazu KatayamaHironobu Hojo
Nov 19, 2011·Carbohydrate Research·Amanda L MattsonMary J Cloninger
Sep 12, 2014·The Journal of Organic Chemistry·Dina Lloyd, Clay S Bennett
Feb 7, 2015·Journal of Colloid and Interface Science·Ligia R Rodrigues

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