Fe(OTf)3 or Photosensitizer-free blue light activated diazo-thioglycoside donors for Iterative and stereoselective glycosylations

Surya Pratap Singh, Umesh Chaudhary, Adrienne Daróczi and Indrajeet Sharma ()
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Surya Pratap Singh: 101 Stephenson Parkway
Umesh Chaudhary: 101 Stephenson Parkway
Adrienne Daróczi: 101 Stephenson Parkway
Indrajeet Sharma: 101 Stephenson Parkway

Nature Communications, 2025, vol. 16, issue 1, 1-12

Abstract: Abstract Conventional methods for thioglycoside activation often rely on precious and toxic platinum group metals. Here, we report a catalytic glycosylation strategy employing diazo-thioglycoside donors activated by earth-abundant iron or photosensitizer-free blue light conditions. It confers orthogonal reactivity relative to most glycosyl donors, including widely used thioglycosides and alkyne-based donors, thereby enabling one-pot orthogonal synthesis of glycans. The Thorpe-Ingold-like effect drives the proximity of iron- or blue-light-generated carbenes to the sulfur atom of thioglycosides. This approach accommodates diverse protecting groups and nucleophiles. It applies to various glycosyl donors derived from glucose, mannose, galactose, rhamnose, xylose, lactose, 2-deoxyamino glucose, and furanose derivatives such as ribose and arabinose. Moreover, we demonstrate the robustness of this methodology through challenging 1,2-cis furanosides, late-stage modifications of biomolecules like cholesterol, and the drug simvastatin on a gram scale, along with the iterative synthesis of challenging hexasaccharides.

Date: 2025
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DOI: 10.1038/s41467-025-56445-1

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