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• W2327883784 endingPage "5744" @default.
• W2327883784 startingPage "5740" @default.
• W2327883784 abstract "The efficient and stereoselective construction of glycosidic linkages remains one of the most formidable challenges in organic chemistry. This is especially true in cases such as β-linked deoxy-sugars, where the outcome of the reaction cannot be controlled using the stereochemical information intrinsic to the glycosyl donor. Here we show that p-toluenesulfonic anhydride activates 2-deoxy-sugar hemiacetals in situ as electrophilic species, which react stereoselectively with nucleophilic acceptors to produce β-anomers exclusively. NMR studies confirm that, under these conditions, the hemiacetal is quantitatively converted into an α-glycosyl tosylate, which is presumably the reactive species in the reaction. This approach demonstrates that use of promoters that activate hemiacetals as well-defined intermediates can be used to permit stereoselective glycosylation through an SN2-pathway." @default.
• W2327883784 created "2016-06-24" @default.
• W2327883784 creator A5009403356 @default.
• W2327883784 creator A5073516019 @default.
• W2327883784 date "2014-04-02" @default.
• W2327883784 modified "2023-10-17" @default.
• W2327883784 title "A Reagent-Controlled S_N2-Glycosylation for the Direct Synthesis of β-Linked 2-Deoxy-Sugars" @default.
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• W2327883784 doi "https://doi.org/10.1021/ja500410c" @default.
• W2327883784 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/24670112" @default.
• W2327883784 hasPublicationYear "2014" @default.
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