Synthesis of 2-nitroglycals from glycals using the tetrabutylammonium nitrate-trifluoroacetic anhydride-triethylamine reagent system and base-catalyzed Ferrier rearrangement of acetylated 2-nitroglycals.
A reagent system comprising tetrabutylammonium nitrate-trifluoroacetic anhydride-triethylamine has been developed for the synthesis of 2-nitroglycals from various protected glycals. The base-catalyzed Ferrier rearrangement on tri-O-acetylated 2-nitroglycals has been reported for the first time. Reactivity of these nitroacetates and associated selectivity has been examined, and some of the products have been converted into 2,3-diamino-2,3-dideoxyglycosides and methyl N-acetyl-D-lividosaminide.
Department of Chemistry, Indian Institute of Technology, Kanpur 208 016, India.
Suresh
S
Dharuman
Preeti
P
Gupta
Pavan K
PK
Kancharla
Yashwant D
YD
Vankar
D000089:Acetic Anhydrides / Q000737:chemistry*; D000107:Acetylation; D002384:Catalysis; D005021:Ethylamines / Q000737:chemistry*; D005463:Fluoroacetates / Q000737:chemistry*; D015394:Molecular Structure; D011134:Polysaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry*; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*
C417980:4-(dimethylamine)pyridine; D000089:Acetic Anhydrides; D005021:Ethylamines; D005463:Fluoroacetates; D011134:Polysaccharides; D011725:Pyridines; D000644:Quaternary Ammonium Compounds; C017958:trifluoroacetic anhydride; C009405:tetrabutylammonium; C016162:triethylamine