Methyl-α-D-2-selenonyl Pent-2-enofuranoside: A Reactive Selenosugar for the Diversity Oriented Synthesis of Enantiomerically Pure Heterocycles, Carbocycles, and Isonucleosides.
The construction of vinyl selenone on a furanoside led to a highly reactive synthetic intermediate methyl-α-D-2-selenonyl pent-2-enofuranoside composed of a masked aldehyde, an electron-deficient double bond along with an excellent leaving group. This new Michael acceptor on reactions with different nucleophiles afforded bicyclic azasugars, cyclopropanated carbohydrate, dihydrofuran- and dihydroisoxazole- substituted furanosides, and isonucleosides in moderate to good yields. Hydrolysis of the hemiacetal linkage of some of these modified carbohydrates afforded enantiopure aziridines, nitrocyclopropane, and dihydrofuran.
Department of Chemistry, Indian Institute of Technology Kharagpur , Kharagpur 721302, India.
Atanu
A
Bhaumik
Department of Chemistry, Indian Institute of Technology Kharagpur , Kharagpur 721302, India.
Tanmaya
T
Pathak