Grignard reagent addition to N-quaternary iminiumcyclitols

CARB 110

Robert M. Moriarty, moriarty@uic.edu1, Carmen I. Mitan, cmitan@uic.edu1, Baohua Gu2, and Timothy Block3. (1) Department of Chemistry, University of Illinois at Chicago, 845 W Taylor St, Room # 4500, Chicago, IL 60607, (2) Drexel University, College of Medicine, Drexel Institute for Biotechnology and Virology Research, 3805 Old Easton Road, Doylestown, 18902, (3) Drexel Institute for Biotechnology and Virology Research, Drexel University, College of Medicine, 3805 Old Easton Road, Doylestown, 18902

Five-membered azasugars possessing N-alkyl and C1 alkyl substituents constitute a class of potent antiviral compounds active against hepatitis B virus (HBV), hepatitis C virus (HCV), and human immunodeficiency virus (HIV). Recently we observed enhanced antiviral activity attendant the presence of both an N-alkyl group as well as a C1 dialkyl group. We report now a general synthesis of five-membered azasugars possessing both N-alkyl group and C1 geminal dialkyl groups. Thus starting with L-lyxonolactone the series of analog I was obtained. Members of the enantiomeric series of compounds have been made in the D-lyxo → L-ribo series (II). The antiviral activity of these new iminocyclitols in the bovine viral diarrhoea virus assay (BVDV) will be presented.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Carbohydrate Synthesis and Mechanism
1:30 PM-5:30 PM, Wednesday, March 28, 2007 McCormick Place North -- Room N226, Level 2, Oral

Division of Carbohydrate Chemistry

The 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007