A synthesis of methyl 4,6-dideoxy-3-C-methyl-4-(N-methylacetamido)-alpha-D-altropyr anoside, the 3-epimer of (methyl N-acetylsibirosaminide).
The oxirane ring of 1,6:3,4-dianhydro-beta-D-talopyranose reacted at C-4 with methylamine, and the product, further processed gave a 3-deoxy-C-3-methylene derivative. Iodonium ion-induced cyclisation led to an iodooxazolidinone, and deiodination, followed by hydrolysis and N-acetylation, to the title compound.
D002855:Chromatography, Thin Layer; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008759:Methylglycosides / Q000138:chemical synthesis*; D009904:Optical Rotation; D013237:Stereoisomerism
D007202:Indicators and Reagents; D008759:Methylglycosides; C042762:methyl N-acetylsibirosaminide