100604-09-9Relevant academic research and scientific papers
Further Syntheses of C-Branched α-Deoxycyclitols Starting from 1,6-Anhydrohexopyranoses
Klemer, Almuth,Kohla, Monika
, p. 967 - 979 (2007/10/02)
1,6-Anhydro-3,4-O-isopropylidene-β-D-altropyranose (4) reacts with n-butyllithium to give 1L-1-C-butyl-2,3-O-isopropylidene-1,2,3,5/4-cyclohexanepentol (5a).The analogous reaction with methyllithium yields the C-methyl-branched cyclitols 5b, 6, and 7.Reaction of 2,7-anhydro-4,5-O-isopropylidene-β-D-sedoheptulopyranose (8) with n-butyllithium gives the di-C-branched cyclitol 9a, whereas with methyllithium the two isomers 9b and 10 are isolated. 1,6-Anhydro-2,3,4-tri-O-methyl-β-D-glucopyranose (11) produces a considerable amount of 2,4-dimethoxyphenol (13) besides the expected C-branched cyclitol 12.The enantiomer of 5a, in terms of the 4-O-methyl derivative 15a, is formed by the reaction of 1,6-anhydro-2-O-methyl-3,4-O-isopropylidene-β-D-galactopyranose (14) with n-butyllithium.Starting from 15a, some additional reactions for C-branched unsaturated cyclitols as well as for aminodeoxycyclitols are described.
