Journal of the Chemical Society. Perkin transactions I p. 57 - 60 (1985)
Update date:2022-08-04
Topics:
Diolez, Christian
Sarfati, S. Robert
Szabo, Ladislas
In acidic medium the oxazoline derived from 2-<(3RS)-3-acetoxytetradecanamido>-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose readily eliminates elements of acetic acid: it is transformed into an oxazoline that carries an olefinic substituent having the E configuration; this compound, when treated with an alcohol, yields the corresponding β-D-glucosaminide.No elimination takes place with the analogous 3-hydroxy- or 3-benzyloxy-tetradecanamidoglucosamine derivatives. (3R)-3-benzyloxy-tetradecanoic acid was obtained in 60percent yield upon treatment of methyl (3R)-3-hydroxytetradecanoate in benzene with benzyl bromide, silver oxide, and anhydrous calcium sulphate, followed by saponification.Under similar conditions 3,4,6-tri-O-acetyl-1,2-dideoxy-4',5'-dihydro-2-<(2R)-2-hydroxytridecyl>-α-D-glucopyranoso<2,1-d>oxazole was transformed into the corresponding (2R)-2-benzyloxyoxazoline.
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