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Solvent Effects in the Nucleophilic Substitutions of Tetrahydropyran Acetals Promoted by Trimethylsilyl Trifluoromethanesulfonate: Trichloroethylene as Solvent for Stereoselective C- and O-Glycosylations
[Image: see text] The selectivities of nucleophilic substitution reactions of tetrahydropyran acetals promoted by trimethylsilyl trifluoromethanesulfonate depend upon the reaction solvent. Polar solvents favor the formation of S(N)1 products, while nonpolar solvents favor S(N)2 products. Trichloroet...
| Autores principales: | , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
American Chemical Society
2014
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| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4334250/ https://www.ncbi.nlm.nih.gov/pubmed/24991982 http://dx.doi.org/10.1021/ol501471c |
| _version_ | 1782358156691636224 |
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| author | Kendale, Joanna C. Valentín, Elizabeth M. Woerpel, K. A. |
| author_facet | Kendale, Joanna C. Valentín, Elizabeth M. Woerpel, K. A. |
| author_sort | Kendale, Joanna C. |
| collection | PubMed |
| description | [Image: see text] The selectivities of nucleophilic substitution reactions of tetrahydropyran acetals promoted by trimethylsilyl trifluoromethanesulfonate depend upon the reaction solvent. Polar solvents favor the formation of S(N)1 products, while nonpolar solvents favor S(N)2 products. Trichloroethylene was identified as the solvent most likely to give S(N)2 products in both C- and O-glycosylation reactions. |
| format | Online Article Text |
| id | pubmed-4334250 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2014 |
| publisher | American Chemical Society |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-43342502015-07-03 Solvent Effects in the Nucleophilic Substitutions of Tetrahydropyran Acetals Promoted by Trimethylsilyl Trifluoromethanesulfonate: Trichloroethylene as Solvent for Stereoselective C- and O-Glycosylations Kendale, Joanna C. Valentín, Elizabeth M. Woerpel, K. A. Org Lett [Image: see text] The selectivities of nucleophilic substitution reactions of tetrahydropyran acetals promoted by trimethylsilyl trifluoromethanesulfonate depend upon the reaction solvent. Polar solvents favor the formation of S(N)1 products, while nonpolar solvents favor S(N)2 products. Trichloroethylene was identified as the solvent most likely to give S(N)2 products in both C- and O-glycosylation reactions. American Chemical Society 2014-07-03 2014-07-18 /pmc/articles/PMC4334250/ /pubmed/24991982 http://dx.doi.org/10.1021/ol501471c Text en Copyright © 2014 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes. |
| spellingShingle | Kendale, Joanna C. Valentín, Elizabeth M. Woerpel, K. A. Solvent Effects in the Nucleophilic Substitutions of Tetrahydropyran Acetals Promoted by Trimethylsilyl Trifluoromethanesulfonate: Trichloroethylene as Solvent for Stereoselective C- and O-Glycosylations |
| title | Solvent Effects in the Nucleophilic Substitutions
of Tetrahydropyran Acetals Promoted by Trimethylsilyl Trifluoromethanesulfonate:
Trichloroethylene as Solvent for Stereoselective C- and O-Glycosylations |
| title_full | Solvent Effects in the Nucleophilic Substitutions
of Tetrahydropyran Acetals Promoted by Trimethylsilyl Trifluoromethanesulfonate:
Trichloroethylene as Solvent for Stereoselective C- and O-Glycosylations |
| title_fullStr | Solvent Effects in the Nucleophilic Substitutions
of Tetrahydropyran Acetals Promoted by Trimethylsilyl Trifluoromethanesulfonate:
Trichloroethylene as Solvent for Stereoselective C- and O-Glycosylations |
| title_full_unstemmed | Solvent Effects in the Nucleophilic Substitutions
of Tetrahydropyran Acetals Promoted by Trimethylsilyl Trifluoromethanesulfonate:
Trichloroethylene as Solvent for Stereoselective C- and O-Glycosylations |
| title_short | Solvent Effects in the Nucleophilic Substitutions
of Tetrahydropyran Acetals Promoted by Trimethylsilyl Trifluoromethanesulfonate:
Trichloroethylene as Solvent for Stereoselective C- and O-Glycosylations |
| title_sort | solvent effects in the nucleophilic substitutions
of tetrahydropyran acetals promoted by trimethylsilyl trifluoromethanesulfonate:
trichloroethylene as solvent for stereoselective c- and o-glycosylations |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4334250/ https://www.ncbi.nlm.nih.gov/pubmed/24991982 http://dx.doi.org/10.1021/ol501471c |
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