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Literature DB >> 19492383

Ketone hydrosilylation with sugar silanes followed by intramolecular aglycone delivery: an orthogonal glycosylation strategy.

Zachary A Buchan¹, Scott J Bader, John Montgomery.

Abstract

Gettin' a little sugar-no alcohol required: A procedure for the direct glycosylation of ketones without a hydroxy intermediate enables the site-selective glycosylation of hydroxyketones at the ketone or the alcohol functionality without the use of protecting groups on the aglycone (see scheme). Site selectivity is controlled by the catalyst structure in hydrosilylation and dehydrogenative silylation reactions with sugar silanes. Bn=benzyl.

Entities: Chemical Gene Species

Mesh：

Substances：

Year: 2009 PMID： 19492383 PMCID： PMC2808036 DOI： 10.1002/anie.200901666

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

21 in total

1. Reductive Samariation of Anomeric 2-Pyridyl Sulfones with Catalytic Nickel: An Unexpected Improvement in the Synthesis of 1,2-trans-Diequatorial C-Glycosyl Compounds.

Authors:
Journal: Angew Chem Int Ed Engl Date: 2000-11-17 Impact factor: 15.336

2. Synthesis of glycopeptides containing carbohydrate and Peptide recognition motifs.

Authors: H Herzner; T Reipen; M Schultz; H Kunz
Journal: Chem Rev Date: 2000-12-13 Impact factor: 60.622

3. A simple and efficient copper-catalyzed procedure for the hydrosilylation of hindered and functionalized ketones.

Authors: Silvia Díez-González; Harneet Kaur; Fabiano Kauer Zinn; Edwin D Stevens; Steven P Nolan
Journal: J Org Chem Date: 2005-06-10 Impact factor: 4.354

4. Site-selective derivatization and remodeling of erythromycin A by using simple peptide-based chiral catalysts.

Authors: Chad A Lewis; Scott J Miller
Journal: Angew Chem Int Ed Engl Date: 2006-08-25 Impact factor: 15.336

Review 5. Intramolecular aglycon delivery.

Authors: Ian Cumpstey
Journal: Carbohydr Res Date: 2008-04-29 Impact factor: 2.104

Review 6. Glycopeptides as versatile tools for glycobiology.

Authors: Therese Buskas; Sampat Ingale; Geert-Jan Boons
Journal: Glycobiology Date: 2006-05-04 Impact factor: 4.313

7. New principles for glycoside-bond formation.

Authors: Xiangming Zhu; Richard R Schmidt
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

8. Copper, silver, and gold complexes in hydrosilylation reactions.

Authors: Silvia Díez-González; Steven P Nolan
Journal: Acc Chem Res Date: 2008-02 Impact factor: 22.384

Review 9. Chemical glycosylation in the synthesis of glycoconjugate antitumour vaccines.

Authors: Danica P Galonić; David Y Gin
Journal: Nature Date: 2007-04-26 Impact factor: 49.962

10. Stereocontrolled photocyclization of 1,2-diketones: application of a 1,3-acetyl group transfer methodology to carbohydrates.

Authors: Antonio J Herrera; María Rondón; Ernesto Suárez
Journal: J Org Chem Date: 2008-03-28 Impact factor: 4.354

7 in total

Review 7. Intramolecular glycosylation.

Authors: Xiao G Jia; Alexei V Demchenko
Journal: Beilstein J Org Chem Date: 2017-09-29 Impact factor: 2.883

7 in total

Ketone hydrosilylation with sugar silanes followed by intramolecular aglycone delivery: an orthogonal glycosylation strategy.

1. Reductive Samariation of Anomeric 2-Pyridyl Sulfones with Catalytic Nickel: An Unexpected Improvement in the Synthesis of 1,2-trans-Diequatorial C-Glycosyl Compounds.

2. Synthesis of glycopeptides containing carbohydrate and Peptide recognition motifs.

3. A simple and efficient copper-catalyzed procedure for the hydrosilylation of hindered and functionalized ketones.

4. Site-selective derivatization and remodeling of erythromycin A by using simple peptide-based chiral catalysts.

Review 5. Intramolecular aglycon delivery.

Review 6. Glycopeptides as versatile tools for glycobiology.

7. New principles for glycoside-bond formation.

8. Copper, silver, and gold complexes in hydrosilylation reactions.

Review 9. Chemical glycosylation in the synthesis of glycoconjugate antitumour vaccines.

10. Stereocontrolled photocyclization of 1,2-diketones: application of a 1,3-acetyl group transfer methodology to carbohydrates.

1. Chemoselective hydrosilylation of hydroxyketones.

2. A streamlined strategy for aglycone assembly and glycosylation.

3. Mechanistic study of nickel-catalyzed ynal reductive cyclizations through kinetic analysis.

4. Reverse orthogonal strategy for oligosaccharide synthesis.

5. Fluoride Migration Catalysis Enables Simple, Stereoselective, and Iterative Glycosylation.

6. Sugar Silanes: Versatile Reagents for Stereocontrolled Glycosylation via Intramolecular Aglycone Delivery.

Review 7. Intramolecular glycosylation.