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- W2020021250 abstract "Abstract 2,5-Diacetamido-1,3-di- O -acetyl-2,5-dideoxy-α- d -xylofuranose, 2,5-diacetamido-1,3-di- O -acetyl-2,5-dideoxy- d -ribofuranose, 2,3,5-triacetamido-1- O -acetyl-2,3,5-trideoxy-α- d -xylofuranose, and 2,3,5-triacetamido-1- O -acetyl-2,3,5-trideoxy-a(and-β)- d -ribofuranose were synthesized from benzyl 2-(benzyloxycarbonylamino)-2-deoxy-β- d -xylofuranoside ( 1 ). The derived p -toluenesulfonate or methanesulfonate underwent displacement with azide ion, to yield, after reduction and acetylation, benzyl 2,5-diacetamido-3- O -acetyl-2,5-dideoxy-β- d -xylofuranoside, or benzyl 2,3,5-triacetamido-2,3,5-trideoxy-β- d -ribofuranoside ( 20 ), respectively. Treatment with sodium acetate of benzyl 2-acetamido-5-azido-3- O -mesyl-β- d -xylofuranoside ( 10 ), prepared from 1 in four steps, gave benzyl 2-acetamido-5-azido-2,5-dideoxy-β- d -ribofuranoside ( 14 ). Reduction of 14 , followed by acetylation, afforded the corresponding 2,5-diaminoribofuranoside derivative. Benzyl 2,3,5-triacetamido-2,3,5-trideoxy-β- d -xylofuranoside ( 13 ) was synthesized by way of an azide-exchange reaction on benzyl 2-acetamido-5-azido-2,5-dideoxy-3- O -mesyl-β- d -ribofuranoside, derived from 14 . Hydrogenation of benzyl 2,5-diacetamido-2,5-dideoxy-β- d -xylofuranoside and 13 , and benzyl 2,5-diacetamido-2,5-dideoxy-β- d -ribofuranoside and 20 , followed by acetylation, gave the title compounds in good yields. Treatment of 10 , or benzyl 2-acetamido-2-deoxy-3,5-di- O -mesyl-β- d -xylofuranoside, derived from benzyl 2-(benzyloxycarbonylamino)-2-deoxy-3,5-di- O -mesyl-β- d -xylofuranoside, with sodium azide afforded 2-methyl-(benzyl 5-azido-2,3,5-trideoxy-β- d -ribofuranosido)-[2,3- d ]-2-oxazoline in good yield. Evidence in support of the structures assigned to the new derivatives is presented." @default.
- W2020021250 created "2016-06-24" @default.
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- W2020021250 modified "2023-09-25" @default.
- W2020021250 title "Synthesis of 2,5-diacetamido-2,5-dideoxy- and 2,3,5-triacet-amido-2,3,5-Trideoxy-d-aldopentofuranose derivatives" @default.
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- W2020021250 doi "https://doi.org/10.1016/s0008-6215(00)85674-8" @default.
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