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

DD Long, RJE Stetz, RJ Nash, DG Marquess…

Index: Long, Daniel D.; Stetz, Rebecca J. E.; Nash, Robert J.; Marquess, Daniel G.; Lloyd, Janet D.; Winters, Ana L.; Asano, Naoki; Fleet, George W. J. Journal of the Chemical Society - Perkin Transactions 1, 1999 , # 8 p. 901 - 908

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Citation Number: 3

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 ...