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pubmed-article:3829042pubmed:abstractTextThe first synthesis of 2,5-anhydro-5-thio-D-allononitrile starting with L-lyxose, via a trifluoromethanesulfonic ester intermediate, has been accomplished. Methods have been developed to achieve a large-scale synthesis of 3,4,5,7-tetra-O-acetyl-2,6-anhydro-D-glycero-D-talo-heptononitrile (5). An improved procedure has been developed to synthesize 2,5-anhydro-3,4,6-tri-O-benzoyl-D-gulononitrile (9). The structures of 5 and the thioamide derivative from 9, 2,5-anhydro-3,4,6-tri-O-benzoyl-D-gulonothioamide, were confirmed by X-ray crystallographic analysis.lld:pubmed
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pubmed-article:3829042pubmed:authorpubmed-author:RobinsR KRKlld:pubmed
pubmed-article:3829042pubmed:authorpubmed-author:WilsonB EBElld:pubmed
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pubmed-article:3829042pubmed:authorpubmed-author:HennenW JWJlld:pubmed
pubmed-article:3829042pubmed:authorpubmed-author:DalleyN KNKlld:pubmed
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pubmed-article:3829042pubmed:pagination81-94lld:pubmed
pubmed-article:3829042pubmed:dateRevised2007-11-14lld:pubmed
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pubmed-article:3829042pubmed:year1987lld:pubmed
pubmed-article:3829042pubmed:articleTitleImproved and large-scale synthesis of certain glycosyl cyanides. Synthesis of 2,5-anhydro-5-thio-D-allononitrile.lld:pubmed
pubmed-article:3829042pubmed:publicationTypeJournal Articlelld:pubmed
pubmed-article:3829042pubmed:publicationTypeResearch Support, U.S. Gov't, P.H.S.lld:pubmed