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Literature DB >> 27566624

TMSOTf mediated stereoselective synthesis of α-C-glycosides from unactivated aryl acetylenes.

Heshan Chen¹, Xiaosheng Luo¹, Saifeng Qiu¹, Wengjie Sun¹, Jianbo Zhang².

Abstract

A metal free and highly stereoselective procedure for the synthesis of 2,3-unsaturated-C-glycosides has been developed between glycals and unactivated aryl acetylenes in the presence of TMSOTf through a triflated C-vinyl glycosides intermediate. The flexibility of the procedure was tested by a wide variety of glycals and unactivated aryl acetylenes (20 examples). The corresponding alkynyl C-glycosides were obtained in good yields with completely α-selectivity in a short time (<25 min). And a plausible mechanism for the synthesis of alkynyl C-glycosides was depicted.

Entities: Chemical

Keywords: Aryl acetylenes; C-glycosides; Glycals; Metal free; TMSOTf

Mesh：

Substances：

Year: 2016 PMID： 27566624 DOI： 10.1007/s10719-016-9718-7

Source DB: PubMed Journal: Glycoconj J ISSN： 0282-0080 Impact factor: 2.916

17 in total

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3. Chemoenzymatic synthesis of novel C-ribosylated naphthoquinones.

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4. Saffloflavonesides A and B, two rearranged derivatives of flavonoid C-glycosides with a furan-tetrahydrofuran ring from Carthamus tinctorius.

Authors: Jun He; Ya-Nan Yang; Jian-Shuang Jiang; Zi-Ming Feng; Pei-Cheng Zhang
Journal: Org Lett Date: 2014-10-21 Impact factor: 6.005

5. Total synthesis of ciguatoxin.

Authors: Akinari Hamajima; Minoru Isobe
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

6. Nucleophilic addition of potassium alkynyltrifluoroborates to D-glucal mediated by BF3 x OEt2: highly stereoselective synthesis of alpha-C-glycosides.

Authors: Adriano S Vieira; Pedro F Fiorante; Thomas L S Hough; Fernando P Ferreira; Diogo S Lüdtke; Hélio A Stefani
Journal: Org Lett Date: 2008-10-23 Impact factor: 6.005

TMSOTf mediated stereoselective synthesis of α-C-glycosides from unactivated aryl acetylenes.

1. Ferrier-type alkynylation reaction mediated by indium.

Review 2. Natural products with maleic anhydride structure: nonadrides, tautomycin, chaetomellic anhydride, and other compounds.

3. Chemoenzymatic synthesis of novel C-ribosylated naphthoquinones.

4. Saffloflavonesides A and B, two rearranged derivatives of flavonoid C-glycosides with a furan-tetrahydrofuran ring from Carthamus tinctorius.

5. Total synthesis of ciguatoxin.

6. Nucleophilic addition of potassium alkynyltrifluoroborates to D-glucal mediated by BF3 x OEt2: highly stereoselective synthesis of alpha-C-glycosides.

7. An efficient method for the synthesis of pyranoid glycals.

8. Facile TMSOTf-catalyzed preparation of 2-deoxy α-O-aryl-D-glycosides from glycosyl acetates.

9. Tandem regio- and diastereo-selective synthesis of halogenated C-vinyl glycosides from unactivated arylacetylenes.

10. Zinc(II) catalyzed conversion of alkynes to vinyl triflates in the presence of silyl triflates.

1. Synthesis of 2-Nitro-2,3-Unsaturated Glycosides by a Nanomagnetic Catalyst Fe₃O₄@C@Fe(III).