D. M. Clode, D. Horton, W. Weckerle
Jul 1, 1976
Citations
0
Influential Citations
47
Citations
Journal
Carbohydrate Research
Abstract
Abstract Methyl 2,3- O -benzylidene-6-deoxy-α- L -mannopyranoside ( 2 ) reacted with butyllithium to give a mixture of 1,5-anhydro-3- C -butyl-1,2,6-trideoxy- L - ribo -hex-1-enitol ( 3 ) and its L - arabino analogue ( 4 ), together with methyl 2,3,6-trideoxy-α- L - erythro -hex-2-enopyranoside ( 5 ). In contrast, the 4- O -methyl analogue ( 8 ) of 2 was converted by butyllithium into methyl 2,6-dideoxy-4- O -methyl-α- L - erythro -hexo-pyranosid-3-ulose ( 9 ), which was further characterized as its oxime 10 . The 4- O -benzyl analogue of 8 , obtained as two separate diastereoisomers ( 6 and 7 ) differing in configuration at C-2 of the dioxolane ring, gave a complex mixture of products on treatment with butyllithium.