✦ LIBER ✦
Stereocontrol by intrinsic antiparallel double repulsion on diacetone-D-glucose template. Diastereoselective synthesis of 3(S)-isothiocyanato-3-deoxy-3-C-vinyl glucose via (3,3)-sigmatropic rearrangement of allylic thiocyanates
✍ Scribed by Jozef Gonda; Miroslava Bednárikova
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 237 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
A stereoselective synthesis of the branched-chain sugar 3(S)-isothiocyanato-3-deoxy-3-Cvinyl glucose via (3,3)-sigmatropie rearrangement of allylie thiocyanates prepared from D-glucose is presented. The side chain at C-4 of the substrates 4-Z, 4-E and 8-E is not a decisive factor for stereocontrol in the (3,3)-sigmatropic rearrangement of allylic thiocyanates, and the 1,2-Oisopropylidene group in each isomer profoundly affects the direction of the rearrangement.