Reaction of glycals with trifluoroacetic anhydride and ammonium nitrate. A novel cleavage reaction of glycals.
After aq. workup (pH>7) of the title reaction mixt., 3,4,6-tri-O-acetyl-D-glucal, 3,4,6-tri-O-acetyl-D-galactal and 3,4-di-O-acetyl-L-rhamnal yielded the following ring cleavage products: (E)-(3R),5-diacetoxy-(4R)-formyloxy-1-nitro-1-pentene (I), (E)-(3S),5-diacetoxy-(4R)-formyloxy-1-nitro-1-pentene...
|Journal Title:||Journal of Organic Chemistry Vol. 51; no. 13; pp. 2617 - 2618|
|Authors:||Pimchit Dampawan, Walter W. Zajac, Dolores Ditrow|
|Application Date:||Dep. Chem.,Villanova Univ.,Villanova,PA,USA.|
Carbohydrates and Sugars Role: RCT (Reactant), RACT (Reactant or reagent) (glycals, reaction of, with trifluoroacetic anhydride and ammonium nitrate)
Alkenes Role: SPN (Synthetic preparation), PREP (Preparation) (nitro, chiral, prepn. of, by cleavage of glycals with trifluoroacetic anhydride and ammonium nitrate)