TY - JOUR
T1 - Preparation of S-glycoside surfactants and cysteine thioglycosides using minimally competent Lewis acid catalysis
AU - Szabó, Lajos Z.
AU - Hanrahan, Dillon J.
AU - Jones, Evan M.
AU - Martin, Erin
AU - Pemberton, Jeanne E.
AU - Polt, Robin
N1 - Funding Information:
We acknowledge support of this research through grants from the NSF/EPA Networks for Sustainable Molecular Design and Synthesis (NSMDS) program ( CHE-1339597 ), the Michael J. Fox Foundation , and the Migraine Research Foundation .
PY - 2016/3/3
Y1 - 2016/3/3
N2 - 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 CHCl 3 at reflux in the presence of a catalytic amount of InBr 3 . 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.
AB - 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 CHCl 3 at reflux in the presence of a catalytic amount of InBr 3 . 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.
KW - Glycolipid
KW - Glycosylated cysteine
KW - InBr
KW - S-glycosidic linkage
KW - Surfactant
KW - Thioglycoside
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U2 - 10.1016/j.carres.2015.12.008
DO - 10.1016/j.carres.2015.12.008
M3 - Article
C2 - 26795078
AN - SCOPUS:84955455910
SN - 0008-6215
VL - 422
SP - 1
EP - 4
JO - Carbohydrate Research
JF - Carbohydrate Research
ER -