Treatment of 2,3:5,6-di-0-isopropylidene-D-mannitol with thionyl chloride followed by oxidation gave the corresponding 1,4-cyclic sulfate. Ring opening of the cyclic sulfate with the anion of ethyl 1,3-dithiane-2-carboxylate, and subsequent acidolysis and unmasking of the thioketal, afforded ethyl 4
✦ LIBER ✦
A new route to 3-deoxy-d-manno2-octulosonic acid: felkin-anh rule in radical chemistry
✍ Scribed by Bernd Giese; Bertrand Carboni; Thomas Göbel; Ralf Muhn; Frank Wetterich
- Book ID
- 104215739
- Publisher
- Elsevier Science
- Year
- 1992
- Tongue
- French
- Weight
- 248 KB
- Volume
- 33
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
Abstmck Arabinosyl mbalt complex 5 and silylated pyravate 6 give under radical condition the chain elongated sugar derivative 7. a precursor of KIWI (4). The intermediite radical 8 reacts stereoselectively with BKCl3 according to the Felkin-Anh rule.
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An efficient route to 3-deoxy-d-manno-2-
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