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- W2079673452 abstract "Abstract 2-Acetamido-5-amino-2,5-dideoxy- d -xylopyranosyl hydrogensulfite ( 11 ) has been synthesized from benzyl 2-(benzyloxycarbonylamino)-2-deoxy-5,6- O -isopro-pylidene-β- d -glucofuranoside ( 1 ). O -Deisopropylidenation of 1 gave the triol 2 , which was converted, via oxidative cleavage at C-5-C-6 and subsequent reduction, into the related benzyl β- d -xylofuranoside derivative ( 3 ). Catalytic reduction of benzyl 2-(benzyloxycarbonylamino)-2-deoxy-5- O -tosyl-β- d -xylofuranoside, derived from 3 by selective tosylation, and subsequent N -acetylation, afforded benzyl 2-acetamido-2-deoxy-5- O -tosyl-β- d -xylofuranoside, which was treated with sodium azide to give the corresponding 5-azido derivative ( 6 ). (Tetrahydropyran-2-yl)ation of the product formed by hydrolysis of 6 gave 2-acetamido-5-azido-2,5-dideoxy-1,3- di- O -(tetrahydropyran-2-yl)- d -xylofuranose ( 9 ). Treatment of 2-acetamido-5-amino-2,5-dideoxy-1,3-di- O -(tetrahydropyran-2-yl)- d -xylofuranose, derived from 9 by reduction, with sulfur dioxide in water gave 11 . Hydrogenation of 6 and subsequent acetylation yielded 3-acetamido-4,5-diacetoxy-1-acetyl- xylo -piperidine. Evidence in support of the structures assigned to the new derivatives is presented." @default.
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- W2079673452 date "1980-04-01" @default.
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- W2079673452 title "Synthesis of a 2-acetamido-5-amino-2,5-dideoxy-d-xylopyranosyl derivative" @default.
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- W2079673452 doi "https://doi.org/10.1016/s0008-6215(00)84865-x" @default.
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