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

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• 作者：Chenault ; H. Keith ; Yang ; Jie ; Taber ; Douglass F.
• 关键词：glycosidation ; lithiation ; natural products ; NMR
• 刊名：Tetrahedron
• 出版年：2000
• 出版时间：June 2, 2000
• 年：2000
• 卷：56
• 期：23
• 页码：3673-3677
• 全文大小：111 K

文摘

α-Deamino-3-(β--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.