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- W2952503542 abstract "A variety of approaches towards the synthesis of lincosamine, a derived portion of the antibiotic lincomycin , are reported. Initial approaches involved the intramolecular delivery of a nitrogen atom ( trichloroacetimidate , trichloroacetylcarbamate , carbamate, 2-amino-2- phenylacetate ) attached to O4 onto C6 of a 6,7-anhydrooctoside. Later approaches, albeit more direct but again largely unsuccessful, involved the Sharpless titanium(IV)-mediated nucleophilic opening of a suitable 6,7-anhydrooctose, and the Sharpless oxyamination and the aziridination of suitable octenoses . As an aid to the structure elucidation of several compounds encountered in this work, single-crystal X-ray structure determinations are reported for methyl 6,7-anhydro-2,3-di-O-benzyl-8-deoxy-α-D-threo-D-galacto-octopyranoside , methyl 6,7-anhydro-2,3-di-O-benzyl-8-deoxy-α-D-threo-D-gluco-octopyranoside and 7-azido-7-deoxy-1,2:3,4-di-O-isopropylidene-β-L-erythro-Dgalacto-octose." @default.
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- W2952503542 date "1990-01-01" @default.
- W2952503542 modified "2023-10-03" @default.
- W2952503542 title "Approaches to the Synthesis of Lincosamine, a Derived Portion of the Antibiotic Lincomycin" @default.
- W2952503542 doi "https://doi.org/10.1071/ch9901657" @default.
- W2952503542 hasPublicationYear "1990" @default.
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