TBAF Effects 3,6-Anhydro Formation from 6‑O‑Tosyl Pyranosides
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 su...
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| Veröffentlicht in: | Organic letters 2020-02, Vol.22 (4), p.1453-1457 |
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| creator | Morrison, Zachary A Nitz, Mark |
| description | 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. |
| doi_str_mv | 10.1021/acs.orglett.0c00045 |
| format | Article |
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| title | TBAF Effects 3,6-Anhydro Formation from 6‑O‑Tosyl Pyranosides |
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