Table · dataset · 2026
Conformational Locking Enables Chemoselective Direct 2‑Deoxyglycosylation of C‑4 Equatorial Glycals under Bi-Catalysis
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We demonstrate the chemoselective 2-deoxyglycosylation of formidable C-4 <i>equatorial</i> glycals enabled by a conformationally constrained protecting-group strategy.
Description
A proof-of-principle for the Bi(OTf)<sub>3</sub>-mediated 2-deoxyglycosylation of <i>trans</i>-fused 3,4-O-TIPDS-protected l-rhamnal, d-glucal, and <i>n</i>-xylal is illustrated using carbohydrates, amino-acids, and bioactive-natural products, providing structurally diverse 2-deoxy and 2,6-dideoxyglycoconjugates.
Mechanistic insights into the distinctive structures of the glycosyl species revealed that conformational locking restricts the accessible <b><sup>5</sup><i>H</i></b><sub><b>4</b></sub> glycal and <sup><b>4</b></sup><b><i>H</i></b><sub><b>3</b></sub> oxocarbenium ion conformations, thereby favoring 1,2-addition and circumventing the Ferrier pathway.
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Where it is published
- DOI doi.org/10.1021/acs.orglett.6c03543.s002 ↗
DOI / persistent id · from figshare com
Catalogue records · 1
- OAI-PMH record api.figshare.com/v2/oai?verb=GetRecord&metadataPrefix=oai_dc&identifier=oai%3Af… ↗
metadata API · from figshare com
Topics
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- Astronomy & Astrophysics · Bioinformatics and computational biology · Chemistry · Computer Science & AI · Earth & Environmental Science · Ecology · Economics & Finance · Engineering · Humanities · Immunology · Life Sciences · Medicine & Health · Ocean & Atmospheric Science · Social Science
Provenance · 1 source records, 19 field assertions
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|---|---|---|---|
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| title | source · figshare com | connector:figshare_com@1.0.0 | /metadata/dc/title |