Cargando…
Investigation of acetyl migrations in furanosides
Standard reaction conditions for the desilylation of acetylated furanoside (riboside, arabinoside and xyloside) derivatives facilitate acyl migration. Conditions which favour intramolecular and intermolecular mechanisms have been identified with intermolecular transesterifications taking place under...
| Autores principales: | , |
|---|---|
| Formato: | Texto |
| Lenguaje: | English |
| Publicado: |
Beilstein-Institut
2006
|
| Materias: | |
| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1592296/ https://www.ncbi.nlm.nih.gov/pubmed/16859550 http://dx.doi.org/10.1186/1860-5397-2-14 |
| _version_ | 1782130392977899520 |
|---|---|
| author | Chevallier, O P Migaud, M E |
| author_facet | Chevallier, O P Migaud, M E |
| author_sort | Chevallier, O P |
| collection | PubMed |
| description | Standard reaction conditions for the desilylation of acetylated furanoside (riboside, arabinoside and xyloside) derivatives facilitate acyl migration. Conditions which favour intramolecular and intermolecular mechanisms have been identified with intermolecular transesterifications taking place under mild basic conditions when intramolecular orthoester formations are disfavoured. In acetyl ribosides, acyl migration could be prevented when desilylation was catalysed by cerium ammonium nitrate. |
| format | Text |
| id | pubmed-1592296 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2006 |
| publisher | Beilstein-Institut |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-15922962006-10-06 Investigation of acetyl migrations in furanosides Chevallier, O P Migaud, M E Beilstein J Org Chem Full Research Paper Standard reaction conditions for the desilylation of acetylated furanoside (riboside, arabinoside and xyloside) derivatives facilitate acyl migration. Conditions which favour intramolecular and intermolecular mechanisms have been identified with intermolecular transesterifications taking place under mild basic conditions when intramolecular orthoester formations are disfavoured. In acetyl ribosides, acyl migration could be prevented when desilylation was catalysed by cerium ammonium nitrate. Beilstein-Institut 2006-07-21 /pmc/articles/PMC1592296/ /pubmed/16859550 http://dx.doi.org/10.1186/1860-5397-2-14 Text en Copyright © 2006, Chevallier and Migaud https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms) |
| spellingShingle | Full Research Paper Chevallier, O P Migaud, M E Investigation of acetyl migrations in furanosides |
| title | Investigation of acetyl migrations in furanosides |
| title_full | Investigation of acetyl migrations in furanosides |
| title_fullStr | Investigation of acetyl migrations in furanosides |
| title_full_unstemmed | Investigation of acetyl migrations in furanosides |
| title_short | Investigation of acetyl migrations in furanosides |
| title_sort | investigation of acetyl migrations in furanosides |
| topic | Full Research Paper |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1592296/ https://www.ncbi.nlm.nih.gov/pubmed/16859550 http://dx.doi.org/10.1186/1860-5397-2-14 |
| work_keys_str_mv | AT chevallierop investigationofacetylmigrationsinfuranosides AT migaudme investigationofacetylmigrationsinfuranosides |