TBAF Effects 3,6-Anhydro Formation from 6-O-Tosyl Pyranosides
| Autor: | Zachary A. Morrison, Mark Nitz |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Organic Chemistry Glycoside 010402 general chemistry Tetrabutylammonium fluoride 01 natural sciences Biochemistry 0104 chemical sciences 3. Good health chemistry.chemical_compound Hydroxylamine chemistry Tosyl Organic chemistry Algal polysaccharides Physical and Theoretical Chemistry Sugar |
| Zdroj: | Organic Letters. 22:1453-1457 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.0c00045 |
| Popis: | 3,6-Anhydro sugars are common structures in algal polysaccharides and occur in the furanodictine and sauropunol natural products. We have found that treatment of 6-O-tosylpyranosides with tetrabutylammonium fluoride provides a mild, high-yielding synthesis of 3,6-anhydro sugars. Using O-glycoside substrates, 3,6-anhydropyranosides are isolated and the use of N,O-dimethyl hydroxylamine glycosides yields 3,6-anhydrofuranosides. Applying this approach, concise synthetic routes to several 3,6-anhydro sugar natural products are reported, including furanodictine A and sauropunols A-D. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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