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Literature DB >> 23233443

Highly stereoselective glycosyl-chloride-mediated synthesis of 2-deoxyglucosides.

Abstract

Cl intermediates: The glycosylation of per-O-benzylated 2-deoxy- and 2,6-dideoxythioglycosides, promoted by the combination of para-toluenesulfenyl chloride (p-TolSCl) and silver triflate (AgOTf), furnished the products in high yields and high stereoselectivity. The glycosyl chloride was the intermediate (see scheme).

Entities: Chemical

Mesh：

Substances：
Chlorides
Glycosides

Year: 2012 PMID： 23233443 DOI： 10.1002/chem.201203418

Source DB: PubMed Journal: Chemistry ISSN： 0947-6539 Impact factor: 5.236

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Cited

12 in total

Review 1. Methods for 2-Deoxyglycoside Synthesis.

Authors: Clay S Bennett; M Carmen Galan
Journal: Chem Rev Date: 2018-06-28 Impact factor: 60.622

2. Pre-activation Based Stereoselective Glycosylations.

Authors: Bo Yang; Weizhun Yang; Sherif Ramadan; Xuefei Huang
Journal: European J Org Chem Date: 2017-12-28

3. Reagent Controlled Direct Dehydrative Glycosylation with 2-Deoxy Sugars: Construction of the Saquayamycin Z Pentasaccharide.

Authors: J Colin Mizia; Clay S Bennett
Journal: Org Lett Date: 2019-07-15 Impact factor: 6.005

Review 4. Synthesis and Glycosidation of Anomeric Halides: Evolution from Early Studies to Modern Methods of the 21st Century.

Authors: Yashapal Singh; Scott A Geringer; Alexei V Demchenko
Journal: Chem Rev Date: 2022-06-08 Impact factor: 72.087

5. Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides.

Authors: Hidehisa Someya; Taiki Itoh; Mebae Kato; Shin Aoki
Journal: J Vis Exp Date: 2018-07-26 Impact factor: 1.355

10. Synthesis of Disaccharide Nucleosides Utilizing the Temporary Protection of the 2',3'-cis-Diol of Ribonucleosides by a Boronic Ester.

Authors: Hidehisa Someya; Taiki Itoh; Shin Aoki
Journal: Molecules Date: 2017-10-01 Impact factor: 4.411

Highly stereoselective glycosyl-chloride-mediated synthesis of 2-deoxyglucosides.

Review 1. Methods for 2-Deoxyglycoside Synthesis.

2. Pre-activation Based Stereoselective Glycosylations.

3. Reagent Controlled Direct Dehydrative Glycosylation with 2-Deoxy Sugars: Construction of the Saquayamycin Z Pentasaccharide.

Review 4. Synthesis and Glycosidation of Anomeric Halides: Evolution from Early Studies to Modern Methods of the 21st Century.

5. Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides.

6. TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals.

7. Palladium-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals.

8. Gold(I)-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals.

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

10. Synthesis of Disaccharide Nucleosides Utilizing the Temporary Protection of the 2',3'-cis-Diol of Ribonucleosides by a Boronic Ester.