A novel glycosyl donor for synthesis of 2-acetamido-4-amino-2,4,6-trideoxy-α-d-galactopyranosides

Add time:08/15/2019    Source:sciencedirect.com

2-Azido-4-benzylamino-4-N-,3-O-carbonyl-2,4,6-trideoxy-d-galactopyranosyl trichloroacetimidate (14) was conveniently prepared in six steps by regioselective introduction of an N-benzyl carbamate at O-3 of 6-deoxy-d-glucal 6, followed by mesylation at O-4. Intramolecular displacement of the leaving group afforded oxazolidinone 11. Azidonitration of the bicyclic glycal 11 gave the glycosyl nitrate anomers 12 in good yield and stereoselectivity. Hydrolysis of the anomeric nitrates under aqueous conditions gave the pyranose 13, which was easily converted into the imidate 14. Glycosylation of cyclohexanol by 14 gave glycosides 16α and 16β in a ratio of 4:1.

We also recommend Trading Suppliers and Manufacturers of 3-azido-4-O-(tert-butyldiMethylsilyl)-3,6-dideoxy-α-D-glucopyranose 1,2-diacetate (cas 107599-49-5). Pls Click Website Link as below: cas 107599-49-5 suppliers

Prev:Synthesis of ([11C]carbonyl)raclopride and a comparison with ([11C]methyl)raclopride in a monkey PET study
Next:3-Azidoazetidines as the first scaffolds for β-amino azetidine carboxylic acid peptidomimetics: azetidine iminosugars containing an acetamido group do not inhibit β-N-acetylhexosaminidases)