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A Phase-Transfer Glucosamination of Phenols Catalyzed by Polyethylene Glycol

“…Only β -glycosides result from the reaction, which was confirmed by the 1 H NMR spectra of the resulting compounds identical to those reported in [2].…”

“…2 We have previously demonstrated a high efficiency of various CEs for the use in the interphase catalytic processes of glycosylation of aromatic compounds in the solid phase-liquid phase system [2][3][4][5]. A closeness of the chemical nature of oligoethylene glycols and CEs allows one to expect their catalytic activity would be comparable with that of macrocyclic polyethers.…”

“…The reaction was carried out in anhydrous acetonitrile as described in [2]. It is evident from the information given in the table that the highest yields were obtained with a 4.5-fold excess of potassium carbonate and 0.05 or 0.01 mol of PEG per mol of substrate.…”

Synthesis and investigation of antimicrobial activity of 8-hydroxyquinoline glucosaminides

“…An effective approach suggested earlier for the aryl β D glucosaminide synthesis by glycosylation of aromatic hydroxyl containing compounds in the phase transfer (PT) catalytic system of solid potassium carbonate anhy drous acetonitrile was used to create O β glycoside link age in compounds (V)-(VII) (scheme) [14][15][16]. The interaction of equimolar amounts of chloride (I), hydroxyl derivatives (II)-(IV) and anhydrous potassium carbonate in the presence of the PT catalyst, 15C5, although it resulted in the target products (V)-(VII), pro vided low yields due to the formation of oxazoline (XI), as well as a series of unidentified products of carbohydrate destruction.…”

Synthesis and Crystal Structure of p-Methoxyphenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-.BETA.-D-glucopyranoside

“…The preparation of the title compound 1 is well-known, 3 but another procedure was developed. Boron trifluoride etherate (5.4 mL, 43 mmol) was added to an ice-cold solution of 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose (10.00 g, 25.7 mmol) and p-methoxyphenol (9.50 g, 76.7 mmol) in dry methylene chloride (180 mL) under an argon atmosphere.…”