Tetrahedron

Total Synthesis of α-Deamino-3-(β-d-glucopyranosyloxy) kynurenine

HK Chenault, J Yang, DF Taber

Index: Chenault, H. Keith; Yang, Jie; Taber, Douglass F. Tetrahedron, 2000 , vol. 56, # 23 p. 3673 - 3677

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Citation Number: 6

Abstract

α-Deamino-3-(β-d-glucopyranosyloxy) kynurenine, a yellow, fluorescent compound isolated from human lens, was synthesized in 8 steps (10% overall yield) from commercially available 3-methoxy-2-nitrobenzaldehyde. Key events included preparation and glucosylation of methyl 4-(3-hydroxy-2-nitrophenyl)-4-oxobutanoate followed by reduction of the nitro group and deprotection.