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Literature DB >> 15469352

Stereospecific synthesis of 1,2-cis glycosides by vinyl-mediated IAD.

Kampanart Chayajarus¹, David J Chambers, Majid J Chughtai, Antony J Fairbanks.

Abstract

[reaction: see text] Stereospecific 1,2-cis glycosylation of 2-O-vinyl thioglycosides, synthesized from the corresponding alcohols by Ir-catalyzed transvinylation with vinyl acetate, is achieved by iodine-mediated tethering of a range of primary and secondary carbohydrate acceptors, followed by intramolecular aglycon delivery (IAD). The use of such an intramolecular glycosylation strategy furnishes the desired alpha-gluco and beta-manno disaccharides in an entirely stereoselective manner.

Entities: Chemical Disease

Year: 2004 PMID： 15469352 DOI： 10.1021/ol048427o

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

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Cited

7 in total

1. Mechanisms of Stereodirecting Participation and Ester Migration from Near and Far in Glycosylation and Related Reactions.

Authors: Asiri A Hettikankanamalage; Robert Lassfolk; Filip S Ekholm; Reko Leino; David Crich
Journal: Chem Rev Date: 2020-07-05 Impact factor: 60.622

2. Methodology development and physical organic chemistry: a powerful combination for the advancement of glycochemistry.

Authors: David Crich
Journal: J Org Chem Date: 2011-10-04 Impact factor: 4.354

3. Mimicry of an HIV broadly neutralizing antibody epitope with a synthetic glycopeptide.

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Journal: Sci Transl Med Date: 2017-03-15 Impact factor: 17.956

4. Discovery, Total Synthesis and Key Structural Elements for the Immunosuppressive Activity of Cocosolide, a Symmetrical Glycosylated Macrolide Dimer from Marine Cyanobacteria.

Authors: Sarath P Gunasekera; Yang Li; Ranjala Ratnayake; Danmeng Luo; Jeannette Lo; Joseph H Reibenspies; Zhengshuang Xu; Michael J Clare-Salzler; Tao Ye; Valerie J Paul; Hendrik Luesch
Journal: Chemistry Date: 2016-05-03 Impact factor: 5.236

Stereospecific synthesis of 1,2-cis glycosides by vinyl-mediated IAD.

1. Mechanisms of Stereodirecting Participation and Ester Migration from Near and Far in Glycosylation and Related Reactions.

2. Methodology development and physical organic chemistry: a powerful combination for the advancement of glycochemistry.

3. Mimicry of an HIV broadly neutralizing antibody epitope with a synthetic glycopeptide.

4. Discovery, Total Synthesis and Key Structural Elements for the Immunosuppressive Activity of Cocosolide, a Symmetrical Glycosylated Macrolide Dimer from Marine Cyanobacteria.

5. Synthesis of Mannosidase-Stable Man₃ and Man₄ Glycans Containing S-linked Manα1→2Man Termini.

6. Dependency of the regio- and stereoselectivity of intramolecular, ring-closing glycosylations upon the ring size.

Review 7. Synthetic and semi-synthetic approaches to unprotected N-glycan oxazolines.

Stereospecific synthesis of 1,2-cis glycosides by vinyl-mediated IAD.

1. Mechanisms of Stereodirecting Participation and Ester Migration from Near and Far in Glycosylation and Related Reactions.

2. Methodology development and physical organic chemistry: a powerful combination for the advancement of glycochemistry.

3. Mimicry of an HIV broadly neutralizing antibody epitope with a synthetic glycopeptide.

4. Discovery, Total Synthesis and Key Structural Elements for the Immunosuppressive Activity of Cocosolide, a Symmetrical Glycosylated Macrolide Dimer from Marine Cyanobacteria.

5. Synthesis of Mannosidase-Stable Man3 and Man4 Glycans Containing S-linked Manα1→2Man Termini.

6. Dependency of the regio- and stereoselectivity of intramolecular, ring-closing glycosylations upon the ring size.

Review 7. Synthetic and semi-synthetic approaches to unprotected N-glycan oxazolines.

5. Synthesis of Mannosidase-Stable Man₃ and Man₄ Glycans Containing S-linked Manα1→2Man Termini.