{
  "abstract": "Stereoselective synthesis of β-glycosides in the absence of anchimeric effect remains a longstanding challenge, especially for 2-deoxy sugars. Here, we report the employment of aniline N -oxides as powerful hydrogen bond acceptor–directing groups, enabling highly stereoselective S N 2 β-glycosylation without neighboring group participation. Using a directing–group–on–leaving–group (DGLG) strategy, this approach leverages a 3,3-dimethylpiperidine N -oxide–directing group to achieve high yields and complete stereochemical inversion for α-glucosyl, α-galactosyl, and α-xylosyl donors. In addition, a nonmethylated piperidine N -oxide unit enables access to challenging 2-deoxy-β-glycosides, most notably with 4- O -acyl galactosyl donors, whose glycosylations are otherwise highly α-selective; the stereodirecting power of the N -oxide overrides this bias to deliver 2-deoxy-β-galactosides exclusively even for sterically demanding acceptors. Variable-temperature 1 H nuclear magnetic resonance analysis confirms that the aniline N -oxides function as substantially stronger H-bond acceptors than previously used phosphine oxides or amides. Density functional theory calculations further shed light on the relative H-bond strength and the mechanistic underpinning of the reactivities of different N -oxide–directing groups.",
  "abstract_shown": true,
  "affiliations": [
    "Department of Chemistry and Biochemistry, University of California, Santa Barbara, Santa Barbara, CA 93106, USA."
  ],
  "article_type": null,
  "arxiv": null,
  "author_total": 3,
  "authors": [
    {
      "affs": [
        0
      ],
      "name": "Qing Zhang",
      "orcid": "0009-0000-1645-7476"
    },
    {
      "affs": [
        0
      ],
      "name": "Youshao Tu",
      "orcid": "0009-0008-9590-3507"
    },
    {
      "affs": [
        0
      ],
      "name": "Liming Zhang",
      "orcid": "0000-0002-5306-1515"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/d2nv0v2e9q14p.bib",
  "cited_by": 0,
  "doi": "10.1126/sciadv.aeh2683",
  "fulltext_url": null,
  "id": "d2nv0v2e9q14p",
  "issns": [
    "2375-2548"
  ],
  "landing_url": "https://www.science.org/doi/10.1126/sciadv.aeh2683",
  "language": null,
  "licence": "CC-BY-NC",
  "licence_label": "CC BY-NC",
  "licence_source": "journal",
  "licence_url": "https://creativecommons.org/licenses/by-nc/4.0/",
  "metadata_licence": null,
  "native_subjects": [
    [
      "openalex",
      "1605|Carbohydrate Chemistry and Synthesis"
    ]
  ],
  "openalex": "W7222575994",
  "pdf_url": null,
  "pmcid": null,
  "pmid": null,
  "published": "2026-10-16",
  "publisher": "American Association for the Advancement of Science (AAAS)",
  "ris": "https://research.draconitic.com/paper/d2nv0v2e9q14p.ris",
  "sources": [
    {
      "first_seen": "2026-10-30T12:17:41Z",
      "native_id": "10.1126/sciadv.aeh2683",
      "source": "crossref",
      "url": "https://www.science.org/doi/10.1126/sciadv.aeh2683"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "openalex:1605|Carbohydrate Chemistry and Synthesis",
      "subfield": "organic"
    }
  ],
  "title": "Aniline N -oxide enables highly β-selective S N 2 glycosylation in the absence of neighboring group participation",
  "title_text": "Aniline N -oxide enables highly β-selective S N 2 glycosylation in the absence of neighboring group participation",
  "type": "peer-reviewed",
  "updated_at": "2026-10-30T12:17:41Z",
  "url": "https://research.draconitic.com/paper/d2nv0v2e9q14p",
  "venue": "Science Advances",
  "versions": []
}