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Literature DB >> 23893796

Cooperative catalysis in glycosidation reactions with O-glycosyl trichloroacetimidates as glycosyl donors.

Yiqun Geng¹, Amit Kumar, Hassan M Faidallah, Hassan A Albar, Ibrahim A Mhkalid, Richard R Schmidt.

Abstract

Thiourea mediates cooperative glycosidation through hydrogen bonding. N,N'-Diarylthiourea as cocatalyst enforces an SN2-type acid-catalyzed glycosidation even at room temperature (see scheme; Bn=benzyl). From O-(α-glycosyl) trichloroacetimidates as glycosyl donors and various acceptors, β-glycosides are preferentially or exclusively obtained.

Entities: Chemical

Keywords: acid-base catalysis; cooperativity; glycosylation; organocatalysis; thiourea

Mesh：

Substances：

Year: 2013 PMID： 23893796 DOI： 10.1002/anie.201302158

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

20 in total

1. Macrocyclic bis-thioureas catalyze stereospecific glycosylation reactions.

Authors: Yongho Park; Kaid C Harper; Nadine Kuhl; Eugene E Kwan; Richard Y Liu; Eric N Jacobsen
Journal: Science Date: 2017-01-13 Impact factor: 47.728

2. Highly Selective β-Mannosylations and β-Rhamnosylations Catalyzed by Bis-thiourea.

Authors: Qiuhan Li; Samuel M Levi; Eric N Jacobsen
Journal: J Am Chem Soc Date: 2020-06-26 Impact factor: 15.419

Review 3. Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges.

Authors: Matteo Panza; Salvatore G Pistorio; Keith J Stine; Alexei V Demchenko
Journal: Chem Rev Date: 2018-06-28 Impact factor: 60.622

Review 4. The Experimental Evidence in Support of Glycosylation Mechanisms at the S_N1-S_N2 Interface.

Authors: Philip Ouma Adero; Harsha Amarasekara; Peng Wen; Luis Bohé; David Crich
Journal: Chem Rev Date: 2018-05-30 Impact factor: 60.622

5. Recent Developments in Stereoselective Chemical Glycosylation.

Authors: Jesse Ling; Clay S Bennett
Journal: Asian J Org Chem Date: 2019-05-02 Impact factor: 3.319

6. Regiodivergent Glycosylations of 6-Deoxy-erythronolide B and Oleandomycin-Derived Macrolactones Enabled by Chiral Acid Catalysis.

Authors: Jia-Hui Tay; Alonso J Argüelles; Matthew D DeMars; Paul M Zimmerman; David H Sherman; Pavel Nagorny
Journal: J Am Chem Soc Date: 2017-06-19 Impact factor: 15.419

Cooperative catalysis in glycosidation reactions with O-glycosyl trichloroacetimidates as glycosyl donors.

1. Macrocyclic bis-thioureas catalyze stereospecific glycosylation reactions.

2. Highly Selective β-Mannosylations and β-Rhamnosylations Catalyzed by Bis-thiourea.

Review 3. Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges.

Review 4. The Experimental Evidence in Support of Glycosylation Mechanisms at the S_N1-S_N2 Interface.

5. Recent Developments in Stereoselective Chemical Glycosylation.

6. Regiodivergent Glycosylations of 6-Deoxy-erythronolide B and Oleandomycin-Derived Macrolactones Enabled by Chiral Acid Catalysis.

7. Catalytic activation of glycosyl phosphates for stereoselective coupling reactions.

Review 8. Recent Advances in Stereoselective Chemical O-Glycosylation Reactions.

Review 9. A propos of glycosyl cations and the mechanism of chemical glycosylation; the current state of the art.

10. Phenanthroline-Catalyzed Stereoretentive Glycosylations.

Cooperative catalysis in glycosidation reactions with O-glycosyl trichloroacetimidates as glycosyl donors.

1. Macrocyclic bis-thioureas catalyze stereospecific glycosylation reactions.

2. Highly Selective β-Mannosylations and β-Rhamnosylations Catalyzed by Bis-thiourea.

Review 3. Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges.

Review 4. The Experimental Evidence in Support of Glycosylation Mechanisms at the SN1-SN2 Interface.

5. Recent Developments in Stereoselective Chemical Glycosylation.

6. Regiodivergent Glycosylations of 6-Deoxy-erythronolide B and Oleandomycin-Derived Macrolactones Enabled by Chiral Acid Catalysis.

7. Catalytic activation of glycosyl phosphates for stereoselective coupling reactions.

Review 8. Recent Advances in Stereoselective Chemical O-Glycosylation Reactions.

Review 9. A propos of glycosyl cations and the mechanism of chemical glycosylation; the current state of the art.

10. Phenanthroline-Catalyzed Stereoretentive Glycosylations.

Review 4. The Experimental Evidence in Support of Glycosylation Mechanisms at the S_N1-S_N2 Interface.