Chemoselective hydration of glycosyl cyanides to C-glycosyl formamides using ruthenium complexes in aqueous media

Unprecedented β-manno type thiodisaccharides with a C-glycosylic function by photoinitiated hydrothiolation of 1-C-substituted glycals

“…Next, the O-perbenzoylated amide-substituted glucal 18 24 was subjected to coupling with 2,3,4,6-tetra-O-acetyl-1-thio--D-galactopyranose (4, Scheme 1). The reaction conditions were the same as those used in the case of the hydrothiolation of amide-substituted galactal 1.…”

C-Glucopyranosyl-1,2,4-triazol-5-ones: synthesis and inhibition of glycogen phosphorylase

“…To obtain 5-β-D-glucopyranosyl-1-phenyl-1,2,4-triazol-3-one, compound 25 was prepared as the starting material (Scheme 2). C-Glucosyl formamide 23 30,31 was converted by oxalyl chloride 32 into the acyl isocyanate 24 which was used without purification for the next reaction with PhNHNH2 to give 25 in very good yield. Towards 3-β-D-glucopyranosyl-1-phenyl-1,2,4-triazol-5-one, intermediate 24 was reacted with Boc-protected PhNHNH2 to give 26.…”

Synthesis and catalytic activity of new, water-soluble mono- and dinuclear ruthenium(II) complexes containing 1,3,5-triaza-7-phosphaadamantane: Study of the effect of the visible light

“…Trans-[RuCl 2 (PTA) 4 ] efficiently catalyzed the hydration of various nitriles, as well. [28] We have also reported on the catalytic application of cis-cis-trans-[RuCl 2 (DMSO) 2 L 2 ] complexes and that of trans-[RuCl 2 (PTA) 4 ] in hydration of various nitriles, [29,30] however, these studies did not include investigation of photochemical effects.…”

“…In several cases [16,22,25,29,30] the catalytically active species was presumed to be a Ru(II)-trisphosphine complex, however to date such species have not been isolated in pure form. Earlier, [Ru(OH 2 ) 3 (PTA) 3 ] 2+ (formed in the reaction of [Ru(OH 2 ) 6 ](tos) 2 and PTA) was characterized in aqueous solution [21] and very recently cis-mer-[Ru(S)Cl 2 (PTA) 3 ] complexes were identified in refluxing solutions of trans-[RuCl 2 (PTA) 4 ] using S = DMSO or CH 3 CN as solvents.…”