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Literature DB >> 12762693

Sequential one-pot glycosylations using 1-hydroxyl and 1-thiodonors.

Jeroen D C Codée¹, Leendert J van den Bos, Remy E J N Litjens, Herman S Overkleeft, Jacques H van Boom, Gijs A van der Marel.

Abstract

[reaction: see text] A novel sequential glycosylation procedure is described that combines the use of 1-hydroxyl and thiodonors. The Ph(2)SO/Tf(2)O-mediated dehydrative condensation of 1-hydroxyl donors with thioglycosides affords in good yield the thiodisaccharides, which in turn can be activated by the same activator system to furnish trisaccharides. The alpha-Gal epitope and a hyaluronan trisaccharide were efficiently assembled in a one-pot procedure.

Entities: Chemical

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Year: 2003 PMID： 12762693 DOI： 10.1021/ol034528v

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

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Cited

10 in total

1. Highly efficient syntheses of hyaluronic acid oligosaccharides.

Authors: Lijun Huang; Xuefei Huang
Journal: Chemistry Date: 2007 Impact factor: 5.236

2. Enhanced diastereoselectivity in beta-mannopyranosylation through the use of sterically minimal propargyl ether protecting groups.

Authors: David Crich; Prasanna Jayalath; Thomas K Hutton
Journal: J Org Chem Date: 2006-04-14 Impact factor: 4.354

3. Chemoenzymatic Syntheses of Tumor-Associated Carbohydrate Antigen Globo-H and Stage-Specific Embryonic Antigen 4.

Authors: Zhen Wang; Michel Gilbert; Hironobu Eguchi; Hai Yu; Jiansong Cheng; Saddam Muthana; Luyuan Zhou; Peng George Wang; Xi Chen; Xuefei Huang
Journal: Adv Synth Catal Date: 2008-08-04 Impact factor: 5.837

4. IMPROVED SYNTHESIS OF 1-BENZENESULFINYL PIPERIDINE AND ANALOGS FOR THE ACTIVATION OF THIOGLYCOSIDES IN CONJUNCTION WITH TRIFLUOROMETHANESULFONIC ANHYDRIDE.

Authors: David Crich; Abhisek Banerjee; Wenju Li; Qingjia Yao
Journal: J Carbohydr Chem Date: 2005 Impact factor: 1.667

Sequential one-pot glycosylations using 1-hydroxyl and 1-thiodonors.

1. Highly efficient syntheses of hyaluronic acid oligosaccharides.

2. Enhanced diastereoselectivity in beta-mannopyranosylation through the use of sterically minimal propargyl ether protecting groups.

3. Chemoenzymatic Syntheses of Tumor-Associated Carbohydrate Antigen Globo-H and Stage-Specific Embryonic Antigen 4.

4. IMPROVED SYNTHESIS OF 1-BENZENESULFINYL PIPERIDINE AND ANALOGS FOR THE ACTIVATION OF THIOGLYCOSIDES IN CONJUNCTION WITH TRIFLUOROMETHANESULFONIC ANHYDRIDE.

5. In situ preactivation strategies for the expeditious synthesis of oligosaccharides: A review.

6. Electrochemical generation of glycosyl triflate pools.

7. Mechanistic studies on a sulfoxide transfer reaction mediated by diphenyl sulfoxide/triflic anhydride.

8. Synthesis and reactivity of 4'-deoxypentenosyl disaccharides.

Review 9. Preactivation-based chemoselective glycosylations: A powerful strategy for oligosaccharide assembly.

Review 10. Mechanistic Investigations into the Application of Sulfoxides in Carbohydrate Synthesis.