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Literature DB >> 15200311

Thioglycuronides: synthesis and application in the assembly of acidic oligosaccharides.

Leendert J van den Bos¹, Jeroen D C Codée, John C van der Toorn, Thomas J Boltje, Jacques H van Boom, Herman S Overkleeft, Gijsbert A van der Marel.

Abstract

[reaction: see text] Partially protected thioglycuronic acids are prepared efficiently by chemo- and regioselective oxidation of the corresponding thioglycosides using the TEMPO/BAIB reagent combination. After esterification, the thioglycuronic acids proved to be useful as both donor and acceptor in sulfonium-mediated condensations toward acidic di- and trisaccharides.

Entities: Chemical Species

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Year: 2004 PMID： 15200311 DOI： 10.1021/ol049380+

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

28 in total

1. A facile method for oxidation of primary alcohols to carboxylic acids and its application in glycosaminoglycan syntheses.

Authors: Lijun Huang; Nardos Teumelsan; Xuefei Huang
Journal: Chemistry Date: 2006-07-05 Impact factor: 5.236

2. Installation of electron-donating protective groups, a strategy for glycosylating unreactive thioglycosyl acceptors using the preactivation-based glycosylation method.

Authors: Youlin Zeng; Zhen Wang; Dennis Whitfield; Xuefei Huang
Journal: J Org Chem Date: 2008-09-23 Impact factor: 4.354

3. Stereoelectronic factors in the stereoselective epoxidation of glycals and 4-deoxypentenosides.

Authors: Laura Alberch; Gang Cheng; Seung-Kee Seo; Xuehua Li; Fabien P Boulineau; Alexander Wei
Journal: J Org Chem Date: 2011-03-18 Impact factor: 4.354

4. Chemical synthesis of syndecan-3 glycopeptides bearing two heparan sulfate glycan chains.

Authors: Keisuke Yoshida; Bo Yang; Weizhun Yang; Zeren Zhang; Jicheng Zhang; Xuefei Huang
Journal: Angew Chem Int Ed Engl Date: 2014-06-30 Impact factor: 15.336

5. Obstacles and solutions for chemical synthesis of syndecan-3 (53-62) glycopeptides with two heparan sulfate chains.

Authors: Weizhun Yang; Keisuke Yoshida; Bo Yang; Xuefei Huang
Journal: Carbohydr Res Date: 2016-10-20 Impact factor: 2.104

6. Preactivation-based, one-pot combinatorial synthesis of heparin-like hexasaccharides for the analysis of heparin-protein interactions.

Authors: Zhen Wang; Yongmei Xu; Bo Yang; Gopinath Tiruchinapally; Bin Sun; Renpeng Liu; Steven Dulaney; Jian Liu; Xuefei Huang
Journal: Chemistry Date: 2010-07-26 Impact factor: 5.236

Thioglycuronides: synthesis and application in the assembly of acidic oligosaccharides.

1. A facile method for oxidation of primary alcohols to carboxylic acids and its application in glycosaminoglycan syntheses.

2. Installation of electron-donating protective groups, a strategy for glycosylating unreactive thioglycosyl acceptors using the preactivation-based glycosylation method.

3. Stereoelectronic factors in the stereoselective epoxidation of glycals and 4-deoxypentenosides.

4. Chemical synthesis of syndecan-3 glycopeptides bearing two heparan sulfate glycan chains.

5. Obstacles and solutions for chemical synthesis of syndecan-3 (53-62) glycopeptides with two heparan sulfate chains.

6. Preactivation-based, one-pot combinatorial synthesis of heparin-like hexasaccharides for the analysis of heparin-protein interactions.

7. Synthesis of Chondroitin Sulfate A Bearing Syndecan-1 Glycopeptide.

8. Modular synthesis of heparan sulfate oligosaccharides for structure-activity relationship studies.

9. New glucuronic acid donors for the modular synthesis of heparan sulfate oligosaccharides.

10. Chemical synthesis of a heparan sulfate glycopeptide: syndecan-1.