A new route to C-glycosyl compounds. Wittig-type reaction promoted by zinc
✍ Scribed by Lydie Dheilly; Catherine Fréchou; Daniel Beaupère; Raoul Uzan; Gilles Demailly
- Publisher
- Elsevier Science
- Year
- 1992
- Tongue
- English
- Weight
- 472 KB
- Volume
- 224
- Category
- Article
- ISSN
- 0008-6215
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Various 1-methylene glucose derivatives afforded after ring closure olefin metathesis cyclic polyethers and C-glycoside precursors.
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## Abstract The treatment of the α‐oxoketene dithioacetal sugar derivatives 2 and 7 with concentrated hydrochloric acid in THF leads to the open‐chain uloses 3 and 8. The reaction mechanism can be rationalized as a retro‐aldol reaction. This rationalization was supported by reacting 2 and 7 with DC