Stereoelectronic Control in Regioselective Carbohydrate Protection
| العنوان: | Stereoelectronic Control in Regioselective Carbohydrate Protection |
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| المؤلفون: | Hai Dong, Wei Liu, Xiaoliang Pan, Yixuan Zhou, Olof Ramström, Feng-Chao Cui, Jing-yao Liu |
| المصدر: | The Journal of Organic Chemistry. 77:1457-1467 |
| بيانات النشر: | American Chemical Society (ACS), 2012. |
| سنة النشر: | 2012 |
| مصطلحات موضوعية: | Steric effects, chemistry.chemical_compound, Nucleophile, Chemistry, Dibutyltin oxide, Stereochemistry, Intramolecular force, Organic Chemistry, Regioselectivity, Organic synthesis, Orthoester, Acyl group |
| الوصف: | Organotin-mediated regioselective protection has been extensively used in organic synthesis for many years. However, the mechanistic origin of the resulting regioselectivity is still not clear. By the comparison of the steric and stereoelectronic effects controlling the geometry of five-membered rings formed from neighboring group participation, from intramolecular acyl group migration, or from orthoester transesterification on pyranoside rings, a theory on the pattern resulting from the reaction with dibutyltin oxide is presented. It is thus suggested that the regioselectivity of organotin-mediated protection is controlled by analogous steric and stereoelectronic effects as in neighboring group participation and acyl group migration, mainly dependent on the stereoelectronic effects of the pyranoside itself, and not related to complex stannylene structures. An organotin protection mechanism is also suggested, emanating from steric and stereoelectronic effects, nucleophilicity, and organotin acyl migration. |
| تدمد: | 1520-6904 0022-3263 |
| الوصول الحر: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::67e67bc539a891468faef048fa019dbfTest https://doi.org/10.1021/jo202336yTest |
| رقم الانضمام: | edsair.doi.dedup.....67e67bc539a891468faef048fa019dbf |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 15206904 00223263 |
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