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Issue 8, 1999
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Open-chain acetonides of D-galactono-1,4-lactone as starting materials for pyrrolidines, azepanes and 5-azidomethyltetrahydrofuran-2-carboxylates: monomers for polyhydroxylated nylon and for tetrahydrofuran carbopeptoids

Abstract

Treatment of D-galactono-1,4-lactone with dimethoxypropane in acetone in the presence of tosic acid forms methyl 2,3:5,6-di-O-isopropylidene-D-galactonate 6 (with only the secondary hydroxy group at C-4 unprotected) and methyl 2,3:4,5-di-O-isopropylidene-D-galactonate 5 (with only the primary hydroxy group at C-6 unprotected) in yields of 20% and 78%, respectively. The value of such easily accessible intermediates is illustrated by the synthesis of 1,4-dideoxy-1,4-imino-D-glucitol 16 (a pyrrolidine), and for the efficient preparation of 6-azido-6-deoxy-D-galactono-1,4-lactone 22. The conversion of 22 to a seven-membered galactonolactam 21 (a tetrahydroxycaprolactam) may provide access to hydroxylated nylon polymers. The galactonolactam 21 has no significant inhibitory effect on a number of glycosidases. Reaction of 22 with triflic anhydride gives two epimeric 5-(azidomethyl)tetrahydrofuran-2-carboxylates which provide starting materials for two series of carbopeptoids, one of which probably has a helical structure and the other a structure reminiscent of a β-turn.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1999, 901-908
Article type
Paper

Open-chain acetonides of D-galactono-1,4-lactone as starting materials for pyrrolidines, azepanes and 5-azidomethyltetrahydrofuran-2-carboxylates: monomers for polyhydroxylated nylon and for tetrahydrofuran carbopeptoids

D. D. Long, R. J. E. Stetz, R. J. Nash, D. G. Marquess, J. D. Lloyd, A. L. Winters, N. Asano and G. W. J. Fleet, J. Chem. Soc., Perkin Trans. 1, 1999, 901
DOI: 10.1039/A809807G

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