دورية أكاديمية
De Novo Enantioselective Synthesis of Hexafluorinated d-Glucose.
| العنوان: | De Novo Enantioselective Synthesis of Hexafluorinated d-Glucose. |
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| المؤلفون: | Depienne S; Department of Organic and Macromolecular Chemistry, Ghent University, Campus Sterre, Krijgslaan 281-S4, 9000 Ghent, Belgium., Fontenelle CQ; School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, U.K., Light ME; School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, U.K., Hecke KV; Department of Chemistry, Ghent University, Campus Sterre, Krijgslaan 281-S3, 9000 Ghent, Belgium., Linclau B; Department of Organic and Macromolecular Chemistry, Ghent University, Campus Sterre, Krijgslaan 281-S4, 9000 Ghent, Belgium.; School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, U.K. |
| المصدر: | The Journal of organic chemistry [J Org Chem] 2024 Sep 13. Date of Electronic Publication: 2024 Sep 13. |
| Publication Model: | Ahead of Print |
| نوع المنشور: | Journal Article |
| اللغة: | English |
| بيانات الدورية: | Publisher: American Chemical Society Country of Publication: United States NLM ID: 2985193R Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1520-6904 (Electronic) Linking ISSN: 00223263 NLM ISO Abbreviation: J Org Chem Subsets: MEDLINE |
| أسماء مطبوعة: | Publication: Columbus Oh : American Chemical Society Original Publication: Easton, Pa. [etc.] |
| مستخلص: | We report a de novo enantioselective synthesis of 2,3,4-trideoxy-2,2,3,3,4,4-hexafluoro-d- glycero -hexopyranose (hexafluorinated d-glucose), an iconic polar hydrophobic glycomimetic. The 12-step synthesis features robust and reproducible chemistry and was achieved by incorporating an asymmetric dihydroxylation step to install the stereogenic center with excellent enantioselectivity (95:5 er ). Virtual enantiopurity (>99.5% ee ) was further reached using a simple crystallization procedure and the absolute confirmation was ascertained by X-ray analysis. The synthetic route also allowed access to the novel hexafluorinated heptose derivative 2,3,4-trideoxy-2,2,3,3,4,4-hexafluoro-l- threo -heptopyranose. |
| تواريخ الأحداث: | Date Created: 20240913 Latest Revision: 20240913 |
| رمز التحديث: | 20240914 |
| DOI: | 10.1021/acs.joc.4c01724 |
| PMID: | 39269924 |
| قاعدة البيانات: | MEDLINE |
Find this issue from the American Chemical Society | تدمد: | 1520-6904 |
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| DOI: | 10.1021/acs.joc.4c01724 |