Syntheses of deoxy analogues of methyl 3,6-di-O-alpha-D-mannopyranosyl-alpha-D-mannopyranoside for studies of the binding site of concanavalin A

• Published in: Carbohydrate research 1995-12, Vol.278 (2), p.271-287
• Main Authors: Oscarson, S, Tedebark, U
• Format: Article
• Language: English
• Subjects: Binding Sites; Carbohydrate Conformation; Carbohydrate Sequence; Concanavalin A - chemistry; Deoxy Sugars - chemical synthesis; Deoxy Sugars - chemistry; Disaccharides - chemical synthesis; Disaccharides - chemistry; Magnetic Resonance Spectroscopy; Mass Spectrometry; Molecular Sequence Data; Molecular Structure; Trisaccharides - chemical synthesis; Trisaccharides - chemistry
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(95)00268-5

All of the monodeoxy analogues of methyl 3,6-di-O-alpha-D-mannopyranosyl-alpha-D-mannopyranoside have been synthesized together with two dideoxy (2,3'- and 4,3'-) analogues. The 2'- and 2"-deoxy functions were introduced by NIS-promoted couplings with 2,3,4-tri-O-acetyl-D-glucal as donor, followed by reduction of the resulting 2'- and 2"-iodo derivatives, whereas the 3'-, 3"-, 4'-, 4"-, 6'-, and 6"-deoxy functions were introduced by using known deoxyglycosyl chlorides as donors in coupling reactions promoted by silver trifluoromethanesulfonate. The 2- and 4-deoxy functions on the central mannose residue were introduced by displacement, using triiodoimidazole and triphenylphosphine, of a hydroxyl group by iodine on suitably protected derivatives followed by reduction of the resulting iodo analogues.