352310-79-3Relevant academic research and scientific papers
C-Glycosylmethylene carbenes: Synthesis of anhydro-aldose tosylhydrazones as precursors; generation and a new synthetic route to exo-glycals
Toth, Marietta,Koever, Katalin E.,Benyei, Attila,Somsak, Laszlo
, p. 4039 - 4046 (2007/10/03)
Acylated anhydro-aldononitriles (glycosyl cyanides) were transformed into anhydro-aldose tosylhydrazones by Raney-nickel reduction in the presence of tosylhydrazine in a one-pot reaction. The configuration of the C=N double bond in these hydrazones was E as proven by 15N-1H coupling constants as well as X-ray crystallography. Thermolysis in refluxing 1,4-dioxane of the sodium salts of the tosylhydrazones obtained by sodium hydride (generally 10 eq.) resulted in the formation of anhydro-1-deoxy-ald-1-enitols (exo-glycals). "Dimeric" N-glycosyl-methyl anhydro-aldose tosylhydrazones could also be isolated when the use of less base caused incomplete deprotonation of the starting compounds. This two-step procedure constitutes a novel, reasonably short synthetic pathway to acylated exo-glycals from the readily available glycosyl cyanides.
exo-Glycals from glycosyl cyanides. First generation of C-glycosylmethylene carbenes from 2,5- and 2,6-anhydroaldose tosylhydrazones
Toth,Somsak
, p. 942 - 943 (2007/10/03)
In a one-pot reaction acylated glycosyl cyanides were transformed with Raney nickel-sodium hypophosphite into 2,5- and 2,6-anhydroaldose tosylhydrazones, which gave exo-glycals under Bamford-Stevens conditions.
