Displacement reactions of acyclic carbohydrate derivatives. Part II. A 1,4-methoxyl group migration following acetal participation: 4-O-methyl-L-lyxose
Abstract
The benzoate displacement reaction on 2,3,5-tri-O-benzyl-4-O-toluene-p-sulphonyl-D-ribose dimethyl acetal gave not the expected 4-O-benzoyl-2,3,5-tri-O-benzyl-L-lyxose dimethyl acetal but the isomeric 1-O-benzoyl-2,3,5-tri-O-benzyl-4-O-methyl-L-lyxose methyl hemiacetal as a consequence of methoxyl group participation and migration. The structure of the product was determined by conversion into the known 4-O-methyl-L-lyxitol (2-O-methyl-L-arabinitol) and into 4-O-methyl-L-lyxose. 4-O-Methyl-D-lyxose has been synthesised.