Glycosides for testing glycosidases: Vinyl, l-ethoxyethyl, and l-ethoxybut-3-enyl d-glucopyranosides

• Published in: Carbohydrate research 1980-12, Vol.87 (1), p.63-70
• Main Authors: Dettinger, Hans-Martin, Lehmann, Jochen, Wallenfels, Kurt
• Format: Article
• Language: English
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/S0008-6215(00)85191-5

The reaction of ethyl vinyl ether and 2,3,4,6-tetra- O-acetyl-β- d-glucopyranose ( 1) in the presence of Hg-(OAc) 2 and toluene- p-sulphonic acid as catalysts yielded the acetylated vinyl, l-ethoxyethyl, and l-ethoxybut-3-enyl glycosides in varying proportions. Crystalline l-ethoxybut-3-enyl 2,3,4,6-tetra- O-acetyl-β- d-glucopyranoside ( 2), vinyl 2,3,4,6-tetra- O-acetyl-α- d-glucopyranoside ( 3), and l-ethoxyethyl 2,3,4,6-tetra- O-acetyl-β- d-glucopyranoside ( 4) were isolated by chromatography. Compound 4 was also prepared by the reaction of 1 with cold acetaldehyde diethyl acetal containing a trace of acetic acid, and its α anomer ( 5) by the reaction of 1 with boiling acetaldehyde diethyl acetal containing a trace of acetic acid. Each deacetylated d-glucoside was cleaved by the corresponding d-glucosidase, to yield d-glucose and either acetaldehyde (from deacetylated 3- 5) or but-3-enal (from deacetylated 2).