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A new approach to the synthesis of optically active pseudo-sugar and pseudo-nucleoside Syntheses of pseudo-alpha-D-arabinofuranose, -cyclaradine, and -1-pseudo-beta-D-arabinofuranosyluracil from D-arabinose



A new approach to the synthesis of optically active pseudo-sugar and pseudo-nucleoside Syntheses of pseudo-alpha-D-arabinofuranose, -cyclaradine, and -1-pseudo-beta-D-arabinofuranosyluracil from D-arabinose



Chemical & Pharmaceutical Bulletin 41(3): 636-638



An optically active pseudo-sugar, pseudo-alpha-D-arabinofuranose, was synthesized from D-arabinose in favorable overall yield by using a stereoselective formation of branched nitropyranose as the key step. Furthermore, two biologically active pseudo-beta-D-arabinofuranosylnucleosides, (+)-cyclaradine and (+)-1-pseudo-beta-D-arabinofuranosyluracil, were synthesized via Michael-type reactions of nucleic acid bases and a nitrocyclopentene derivative which was prepared from a synthetic intermediate of pseudo-D-arabinofuranose.

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Accession: 029693769

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DOI: 10.1248/cpb.41.636


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