Stereocontrolled syntheses of deoxyribonucleosides via photoinduced electron-transfer deoxygenation of benzoyl-protected ribo-and arabinonucleosides
Z Wang, DR Prudhomme, JR Buck…
Index: Wang, Zhiwei; Prudhomme, Daniel R.; Buck, Jason R.; Park, Minnie; Rizzo, Carmelo J. Journal of Organic Chemistry, 2000 , vol. 65, # 19 p. 5969 - 5985
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Citation Number: 40
Abstract
The stereocontrolled, de novo syntheses of β-2'-deoxy-, α-2'-deoxy-, β-3'-deoxy-, and β-2', 3'- dideoxyribonucleosides are described. Strategically protected ribose, arabinose, and xylose glycosylation precursors were synthesized bearing C2-esters capable of directing Vorbrüggen glycosylation. The key step is the regioselective deoxygenation of the desired hydroxyl group as either the benzoyl-or 3-(trifluoromethyl) benzoyl derivative. This ...
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