34698-24-3Relevant academic research and scientific papers
Direct carbohydrate to carbocycle conversions via intramolecular allylation with Et2Zn/Pd(0)
Aurrecoechea, José M.,Arrate, Mónica,Gil, Jesús H.,López, Beatriz
, p. 5515 - 5522 (2007/10/03)
Treatment of 5-vinylpyranosides with Et2Zn and catalytic Pd(0), in the presence of ZnCl2, results in the formation of 5-membered carbocyclic products. This carbohydrate ring-contraction features an intramolecular allylation of a ring-opened carbohydrate aldehyde by an in situ-generated nucleophilic allylzinc species. The stereoselectivity about vinyl and free hydroxyl groups at the newly created stereogenic centers varies from low to moderate while both its extent and sense are found to depend on particular structural features (e.g. the configuration of the starting carbohydrate).
SYNTHESIS OF 1,2-O-CYANOETHYLIDENE DERIVATIVES OF ALKYL GLYCOPYRANURONATES BY OXIDATION OF THE 6-TRITYL ETHERS OF THEIR HEXOSE ANALOGUES
Betaneli, Vitali I.,Ott, Andrej Ya.,Brukhanova, Olga V.,Kochetkov, Nikolay K.
, p. 37 - 50 (2007/10/02)
The synthesis of 1,2-O-cyanoethylidene derivatives (CED) of alkyl glycopyranuronates with the D-Glc, D-Gal, and D-Man configurations is described by oxidation of the 3,4-di-O-acetyl-6-O-trityl-CED-hexose analogues with the Jones reagent .The isopropylidenation of hydroxyl-containing triphenylmethyl ethers is demonstrated.
