An asymmetric approach to 2-deoxynucleosides via organosulfur building blocks as chemical chameleons.
An asymmetric synthesis of 6-N-benzoyl-5'-O-benzyl-2'-deoxyadenosine and its a anomer from non-carbohydrate building blocks is achieved in 7 steps. The sequence builds the basic structures using bis(methylthio)methane and methylthiomethyl phenyl sulfone as both nucleophilic and electrophilic building blocks, a feature that suggests their behavior as chemical chameleons. The asymmetric induction is achieved utilizing a kinetic resolution based upon catalytic asymmetric epoxidation.
Trost
B M
BM
Department of Chemistry, Stanford University, California 94305.
Nübling
C
C
D055598:Chemical Phenomena; D002621:Chemistry; D003839:Deoxyadenosines / Q000737:chemistry; D003853:Deoxyribonucleosides / Q000138:chemical synthesis*; D004852:Epoxy Compounds; D009682:Magnetic Resonance Spectroscopy; D008722:Methods; D015394:Molecular Structure; D013237:Stereoisomerism; D013455:Sulfur
D003839:Deoxyadenosines; D003853:Deoxyribonucleosides; D004852:Epoxy Compounds; C065903:6-N-benzoyl-5'-O-benzyl-2'-deoxyadenosine; D013455:Sulfur