The synthesis of allyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-alpha-D-glucopyranoside and of chitobiose derivatives by the oxazoline procedure.
Controlled, partial benzylation of allyl 2-acetamido-3-O-benzyl-2-deoxy-alpha-D-glucopyranoside gave a mixture of the 3,4-di-, 3,6-di- (15), and 3,4,6-tri-O-benzyl derivatives, the major product being 15. Condensation of 15 with 2-methyl-(3,4,6-tri-O-acetul-1,2-dideoxy-alpha-D-glucopyrano)-[2,1-d]-2-oxazoline gave a disaccharide which, after purification, removal of the allyl group, and hydrogenolysis of the benzyl substituents, gave 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-i-deoxy-beta-D-glucopyranosyl)-2-deoxy-alpha-D-glucopyranose. This compound was further converted into di-N-acetyl-hexa-O-acetylchitobiose by acetylation, or into 2-methyl-[4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl)-3,6-di-O-acetyl-1,2-di-deoxy-alpha-D-glucopyrano]-[2,1-d]-2-oxazoline, a starting material for the preparation of di-N-acetyl-alpha-chitobiosyl phsophate.
D004187:Disaccharides / Q000138:chemical synthesis*; D005960:Glucosides / Q000138:chemical synthesis*; D006027:Glycosides / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008722:Methods; D009844:Oligosaccharides / Q000138:chemical synthesis*; D009904:Optical Rotation; D010080:Oxazoles; D013055:Spectrophotometry, Infrared
D004187:Disaccharides; D005960:Glucosides; D006027:Glycosides; D009844:Oligosaccharides; D010080:Oxazoles