The application of the intermediate 2-methyl-glyco-[2,1-d]-2-oxazolines for glycoside synthesis

Factors Affecting Stereocontrol during Glycosidation of 2,3-Oxazolidinone-Protected 1-Tolylthio-N-acetyl-d-glucosamine

“…To confirm these disaccharide products were β-linked thioglycoside donor 1 was coupled to acceptor 3e using PST activation to provide α-linked disaccharide 5 ( J 1,2 = 2.7 Hz) . Acetylation of oxazolidinone 5 provided α-linked N -acetyl derivative 4e, which was identical in all respects to the minor isomer (α) obtained during glycosidation of 3e …”

Copper(II)‐Mediated Activation of Sugar Oxazolines: Mild and Efficient Synthesis of β‐Glycosides of N ‐Acetylglucosamine

“…The 1 H and 13 C NMR spectroscopic data were in agreement with those published. [28] Isopropyl 2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (13): Oxazoline 5 (523 mg, 1.59 mmol) and anhydrous CuCl 2 (222 mg, 1.59 mmol) were coevaporated with toluene. Anhydrous CHCl 3 (3 mL) and anhydrous 2-propanol 12 (496 µL, 6.5 mmol) were then added and the resulting mixture was refluxed for 2 h. After cooling to room temp., the mixture was diluted with acetone (ca.…”