dl-Isoserine and related compounds

TM Williams, R Crumbie…

Index: Williams, Theresa M.; Crumbie, Robyn; Mosher, Harry S. Journal of Organic Chemistry, 1985 , vol. 50, # 1 p. 91 - 97

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Citation Number: 35

Abstract

Syntheses of dl-isoserine (3-amino-2-hydroxypropanoic acid, 7) and further functionalized derivatives are described. Reaction of glyoxylic acid with nitromethane gives the known 2- hydroxy-3-nitropropanoic acid (8), which upon hydrogenolysis affords dl-isoserine in high yield. The comparable nitro-aldol reaction of 3-nitropropanal ethylene acetal (2) with glyoxylic acid produces 2-hydroxy-3-nitro-5-oxopentanoic acid ethylene acetal (4a) as a ...

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