A new and concise synthesis of 3-deoxy-D-arabino-2-heptulopyranosonic acid (DAH) and derivatives through the radical chemistry of Barton esters
作者： Derek H.R. Barton , Wansheng Liu
DOI: 10.1016/S0040-4039(96)02331-3
关键词: Barium salt 、 Chemistry 、 Yield (chemistry) 、 Radical 、 Ethyl ester 、 Hydrolysis 、 Aqueous solution 、 Olefin fiber 、 Organic chemistry
摘要: Abstract Barton ester-based radical chemistry was applied in the synthesis of 3-deoxy-D- arabino -2-heptulopyranosonic acid ( DAH ) from commercial D-ribonolactone. The reaction with olefin 2 , followed by aqueous work-up, provided seven-carbon sugar compounds 5 and 6 (3:1) 60% yield. Removal isopropylidene groups hydrolysis ethyl ester yielded barium salt quantitatively.
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