Synthesis of β-Glycosyl Amides from N-Glycosyl Dinitrobenzenesulfonamides

Abstract

The N-glycosyl-2,4-dinitrobenzenesulfonamides were accessed via benzoyl-protected β-glycosyl azides. The azides were reduced with Adams’ catalyst to the corresponding amines. The glycosylamines were sulfonated with 2,4-dinitrobenzenesulfonyl chloride to form N-glycosyl-2,4-dinitrobenzenesulfonamides in moderate yields. β-Glycosyl amides were then prepared in 67 – 81 % yields by treatment of the sulfonamides with thioacetic acid and cesium carbonate. The conversion of the glycosylsulfonamide to the glycosyl amide proceeded with high stereoselectivity.

Synthesis of a Poly-hydroxypyrolidine-Based inhibitor of Mycobacterium tuberculosis GlgE

“…Synthesis of p-Methylphenyl 2,3,4,6-Tetra-O-benzyl-1thio-β-D-glucopyranoside (14). 12 To synthesize the thioglycosyl donor 14, D-glucose (10) was peracetylated with acetic anhydride followed by glycosylation with p-thiocresol and boron trifluoride diethyl etherate to generate a peracetylated thioglycosyl donor 11 with 85% yield (Scheme 2). Subsequent deacetylation under Zempleń conditions afforded tetraol 13, which was then benzylated to afford the desired pmethylphenyl-2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside (14).…”

Synthesis and Screening of α-Xylosides in Human Glioblastoma Cells

“…1 H and 13 C NMR and HPLC confirmed pure α- (Scheme , compound 3A ) and β-azides (Scheme , compound 3B ). The α-isomer was distinguished from the β-partner based on the differences in the chemical shift and coupling constant of the anomeric protons: δ 5.88 ppm, 3 J H‑1,H‑2 = 3.8 Hz equatorial-axial coupling for compound 3A and δ 4.98 ppm, 3 J H‑1,H‑2 = 7.5 Hz, axial–axial coupling for compound 3B (Figure A, B). , The dihedral angle θ between H-1 and H-2 dictates the proton–proton coupling constant 3 J in compounds 3A and 3B . The anomeric effect in the α-isomer (compound 3A ) shifts the anomeric proton downfield.…”

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2011–2012

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