Oxazoline synthesis of 1,2- trans-2-acetamido-2-deoxyglycosides. Glycosylation of secondary hydroxyl groups in partially protected saccharides

• Published in: Carbohydrate research 1970-10, Vol.15 (1), p.21-27
• Main Authors: Zurabyan, S.E., Antonenko, T.S., Khorlin, A.Ya
• Format: Article
• Language: English
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/S0008-6215(00)80289-X

2-Methyl-glyco[1′,2′:4,5]-2-oxazolines have been used for the glycosylation of partially protected saccharides having a free secondary hydroxyl group. By the oxazoline method, β- d-Glc pNAc-(1→2)-glycerol ( 4), α- d-Man pNAc-(1→2)-glycerol (6), β- d-Glc pNAc-(1→3)- d-Glc ( 8), and β- d-Glc pNAc-(1→3)- d-GlcNAc ( 10) have been synthesized in high yield. Disaccharide 10 was converted into 2-methyl-4,5-[3- O-(2-acetamido-3,4,6-tri- O-acetyl-2-deoxy-β- d-glucopyranosyl)-4,6-di- O-acetyl-α- d-glucopyrano]-2-oxazoline (11) which was then used in the synthesis of the trisaccharide derivative β- d-Glc pNAc-(1→3)-β- d-Glc pNAc-(1→6)-β- d-Glc pNAc-(1→O)-C 6H 4NO 2- p ( 13).