Site‐Selective O‐Arylation of Glycosides

Shang, Weidong; Mou, Ze-Dong; Tang, Hua; Zhang, Xia; Liu, Jie; Fu, Zhen‐Guo; Niu, Dawen

doi:10.1002/ange.201710310

Cited by 8 publications

(1 citation statement)

References 90 publications

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“…Having multiple hydroxyl groups, regioselective functionalization is one of the most challenging problems in carbohydrate synthesis . Selective hydroxyl group protection is as essential as the glycosylation reaction in carbohydrate synthesis, as it offers tailored glycosyl donors and acceptors and useful synthetic intermediates …”

Section: Introductionmentioning

confidence: 99%

Effective Organotin-Mediated Regioselective Functionalization of Unprotected Carbohydrates

et al. 2023

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Regioselective functionalization of unprotected carbohydrates at a secondary OH group in the presence of primary OH groups based on the commonly used organotin-mediated reaction has been improved. We found that the preactivation of the dibutylstannylene acetal intermediate with tetrabutylammonium bromide in toluene is a key to the improved condition for the efficient, high-yielding, and regioselective tosylation, benzoylation, or benzylation of unprotected carbohydrates. The counteranion of tetrabutylammonium ion with a weak coordination ability plays a crucial role in the improved regioselective reactions. A convenient access to the intermediates of synthetic value is also demonstrated in the organotin-mediated regioselective tosylation of unprotected carbohydrates, followed by the nucleophilic inversion reaction to give sulfur-containing and azide-modified carbohydrates.

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Section: Introductionmentioning

confidence: 99%

Effective Organotin-Mediated Regioselective Functionalization of Unprotected Carbohydrates

et al. 2023

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A Chiral Copper Catalyzed Site‐Selective O‐Alkylation of Carbohydrates

et al. 2021

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Highly regioselective alkylation of sugar hydroxyl groups has always been an important challenge in carbohydrate chemistry, especially for the selective alkylation of trans diols, there is no direct and efficient catalytic method so far. A chiral copper catalyzed universal highly site‐selective alkylation of trans‐diols method is realized. This reaction is performed under mild conditions and has broad substrate scope. The selectivity of the reactions can be controlled by adjusting the copper reagents and the chiral ligands. This method was also applied to the site‐selective modification of drugs and natural products.

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Generation of Glycosyl Radicals from Glycosyl Sulfoxides and Its Use in the Synthesis ofC‐linked Glycoconjugates

Shang

Shi

et al. 2020

Angewandte Chemie

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We here report glycosyl sulfoxides appended with an aryl iodide moiety as readily available,air and moisture stable precursors to glycosyl radicals.These glycosyl sulfoxides could be converted to glycosyl radicals by way of arapid and efficient intramolecular radical substitution event. The use of this type of precursors enabled the synthesis of various complex Clinked glycoconjugates under mild conditions.T his reaction could be performed in aqueous media and is amenable to the synthesis of glycopeptidomimetics and carbohydrate-DNA conjugates. Scheme 1. a) Glycosyl radicals as valuable intermediates in C-glycoside synthesis. b) Our strategy to generate glycosyl radicals.

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Site‐Selective O‐Arylation of Glycosides

Cited by 8 publications

References 90 publications

Effective Organotin-Mediated Regioselective Functionalization of Unprotected Carbohydrates

Effective Organotin-Mediated Regioselective Functionalization of Unprotected Carbohydrates

A Chiral Copper Catalyzed Site‐Selective O‐Alkylation of Carbohydrates

Generation of Glycosyl Radicals from Glycosyl Sulfoxides and Its Use in the Synthesis ofC‐linked Glycoconjugates

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