Sulfonamidoglycosylation of methyl ribofuranosides: a novel approach to furanosylsulfonamides

Acylsulfonamide safety-catch linker: promise and limitations for solid–phase oligosaccharide synthesis

“…In both instances, surprisingly, only N -glycoside 20 (minor product) and glycosylated linker 21 (major product) rather than the desired product 22 were found (Scheme 3). N -Glycosidic sulfonamides were previously used during the synthesis of inhibitors of hepatocellular carcinoma cells [26]. This observation illustrates a limitation of the linker system since these undesired reactions result in the preactivation of the safety-catch linker, which can lead to cleavage in presence of nucleophiles.…”

An Overview on the ChemicalN‐Functionalization of Sugars and Formation ofN‐Glycosides

“…Then in 2005 Colinas reported the synthesis of sulfonamidoribofuranosides 168 , from benzylated methyl glycoside 166 using boron trifluoride etherate as catalyst in DCM at room temperature (Scheme ). Methyl glycosides are very sensitive to create an oxocarbenium ion at C (1) in presence of Lewis acid and addition of a sulfonamide afforded the sulfonamidoglycoside 168 .…”

“…Unfortunately, a highly toxic nature of boron trifluoride etherate becomes one of the major drawbacks of this methodology. In order to overcome this drawback, they further study on it and in 2008[68b] come up with new protocol in which they replace the previous catalyst with an inexpensive, nontoxic, and recyclable catalyst HClO 4 ‐SiO 2 . The same reaction using HClO 4 ‐SiO 2 catalyst furnished the corresponding sulfonamidoglycosides with good to high yields with minimal workup and short reaction times.…”

Experimental and theoretical study of the conformational, vibrational and magnetic properties of 4,6-di-O-acetyl-2,3-dideoxy-d-threo-hex-2-enopyranosyl ethanesulfonamide

“…Sulfonamide glycosides have been prepared by sulfonamidoglycosylation of benzylated glycals [1] and methyl glycosides [3] or by Ferrier sulfonamidoglycosylation of acetylated glycals [4]. The last methodology afforded 2,3-dideoxy-D-hex-2-enopyranosyl sulfonamides as an anomeric mixture, in which a anomers were produced predominantly.…”