Chemical synthesis study demonstrates direct 2-deoxyglycosylation of C-4 equatorial glycals using conformational locking, highlighting a versatile route to diverse 2-deoxyglycoconjugates.
We demonstrate the chemoselective 2-deoxyglycosylation of formidable C-4 equatorial glycals enabled by a conformationally constrained protecting-group strategy. A proof-of-principle for the Bi(OTf)3-mediated 2-deoxyglycosylation of trans-fused 3,4-O-TIPDS-protected l-rhamnal, d-glucal, and n-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 5H4 glycal and 4H3 oxocarbenium ion conformations, thereby favoring 1,2-addition and circumventing the Ferrier pathway.
No takes yet. Share an insight, caveat, or question.
Yadav et al. (2026) studied this question.
Synapse has enriched 5 closely related papers on similar clinical questions. Consider them for comparative context: