# Iron-Catalyzed Stereospecific Heterocycle N‑Glycosylation with Glycal Epoxides

**Authors:** Xiao-Wen Zhang, Dakang Zhang, Zixiang Jiang, Hao Xu

PMC · DOI: 10.1021/acs.orglett.5c05451 · Organic Letters · 2026-02-20

## TL;DR

A new iron-catalyzed method enables efficient and stereospecific N-glycosylation of heterocycles with glycal epoxides, offering useful building blocks for drug discovery.

## Contribution

An iron-catalyzed stereospecific N-glycosylation method for glycal epoxides with high yields and low catalyst loadings.

## Key findings

- The method achieves high yields with low catalyst loadings.
- It is functional-group-tolerant and works for complex glycal epoxides and heterocycles.

## Abstract

Stereospecific N-glycosylation
of heterocycles with glycal epoxides
could readily provide valuable building blocks for drug discovery,
but heterocycle N-glycosylation with a pyranose-based glycal epoxide
is still difficult using existing methods. We report herein an iron-catalyzed
stereospecific heterocycle N-glycosylation method for these glycal
epoxides in high yields with low catalyst loadings. This method is
functional-group-tolerant and effective for a wide variety of functionalized,
complex glycal epoxides and heterocycles.

## Linked entities

- **Chemicals:** iron (PubChem CID 23925)

## Full-text entities

- **Diseases:** infectious diseases (MESH:D003141)
- **Chemicals:** BSTFA (MESH:C103255), acetonitrile (MESH:C032159), C (MESH:D002244), guanine (MESH:D006147), glycan (MESH:D011134), uracil (MESH:D014498), lactose (MESH:D007785), CH2Cl2 (MESH:D008752), N (MESH:D009584), glucals (MESH:D002125), sugar (MESH:D000073893), galactals (MESH:C002038), methanol (MESH:D000432), oxone (MESH:C048813), pyrimidine (MESH:C030986), hemin (MESH:D006427), benzimidazole (MESH:C031000), tetrazole (MESH:C045574), adenines (MESH:D000225), indazole (MESH:D007191), disaccharide (MESH:D004187), Iron (MESH:D007501), ribavirin (MESH:D012254), Lewis acid (MESH:D058116), imidazole (MESH:C029899), cytosines (MESH:D003596), gougerotin (MESH:C004942), acetone (MESH:D000096), 3-isoadenosine (MESH:C062751), toluene (MESH:D014050), 1,2,4-Triazoles (MESH:C045575), ZnCl2 (MESH:C016837), glucuronic-acid (MESH:D020723), benzimidazoles (MESH:D001562), GlcN)-alpha-1,6-glucose (-), 1,4-Dioxane (MESH:C025223), maltose (MESH:D008320), glucosamine ( (MESH:D005944), epoxide (MESH:D004852), nucleoside (MESH:D009705), purine (MESH:C030985), triazole (MESH:D014230)
- **Species:** Human betaherpesvirus 5 (no rank) [taxon 10359]

## Full text

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## Figures

6 figures with captions in the complete paper: https://tomesphere.com/paper/PMC12949690/full.md

## References

50 references — full list in the complete paper: https://tomesphere.com/paper/PMC12949690/full.md

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Source: https://tomesphere.com/paper/PMC12949690