Synthetic explorations towards 3-deoxy-3-fluoro derivatives of d-perosamine
| Autor: | Emmanuel Poirot, Pavol Kováč, Derek Horton, Alex H. C. Chang |
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| Rok vydání: | 2001 |
| Předmět: |
Magnetic Resonance Spectroscopy
Diethylamines Molecular Structure Perosamine Chemistry Stereochemistry Organic Chemistry O Antigens Fluorine General Medicine Methylation Nuclear magnetic resonance spectroscopy Biochemistry Analytical Chemistry law.invention Diethylaminosulfur trifluoride chemistry.chemical_compound law Molecule Indicators and Reagents Mannose Vibrio cholerae Walden inversion |
| Zdroj: | Carbohydrate Research. 334:195-205 |
| ISSN: | 0008-6215 |
| Popis: | Based on a literature precedent, preparation of methyl 4-azido-3,4,6-trideoxy-3-fluoro-alpha-D-mannopyranoside (18) was attempted via fluorination of methyl 4-azido-2-O-benzyl-4,6-dideoxy-alpha-D-altropyranoside with diethylaminosulfur trifluoride (DAST). Contrary to expectations, the reaction took place with retention of configuration at the site of the fluorination yielding methyl 4-azido-2-O-benzyl-3,4,6-trideoxy-3-fluoro-alpha-D-altropyranoside. Treatment with DAST of methyl 4-azido-2-O-benzyl-4,6-dideoxy-alpha-D-allopyranoside (8), or its 2-(p-methoxybenzyl) analog 9 resulted in fluorination with inversion of configuration at position 3, to give the corresponding 3-deoxy-3-fluoro glucopyranosides 10 and 11, respectively. Accordingly, compound 18 was prepared from 11, by de-p-methoxybenzylation at O-2, followed by inversion of configuration at C-2 in the resulting methyl 4-azido-3,4,6-trideoxy-3-fluoro-alpha-D-glucopyranoside. The 2-O-methyl analog of 18 (19) was prepared by methylation of 18. Compounds 18 and 19 were converted, conventionally, into the 3-fluoro analogs of the terminal determinants of the O-PS of Vibrio cholerae O:1, serotype Inaba and Ogawa, respectively. |
| Databáze: | OpenAIRE |
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