Imino-C-nucleoside synthesis: heteroaryl lithium carbanion additions to a carbohydrate cyclic imine and nitrone.
Promotion by Lewis acid of the addition of some aryllithiums to a carbohydrate-based imine, which has allowed a more facile synthesis of some imino-C-nucleoside analogues, is described. Use of the corresponding nitrone does not assist in some cases, but lithiated acetonitrile adds to it efficiently to give a product from which further C-nucleoside analogues can be derived.
Evans
Gary B
GB
Carbohydrate Chemistry, Industrial Research Limited, P.O. Box 31310, Lower Hutt, New Zealand.
Furneaux
Richard H
RH
Hausler
Herwig
H
Larsen
Janus S
JS
Tyler
Peter C
PC
D000097:Acetonitriles / Q000737:chemistry; D000840:Anisoles / Q000737:chemistry; D002241:Carbohydrates / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D007097:Imines / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D009589:Nitrogen Oxides / Q000737:chemistry*; D009705:Nucleosides / Q000138:chemical synthesis*; D009942:Organometallic Compounds / Q000737:chemistry*; D013696:Temperature; D017971:Tin Compounds
D000097:Acetonitriles; D000840:Anisoles; D002241:Carbohydrates; D004987:Ethers; D006571:Heterocyclic Compounds; D007097:Imines; D009589:Nitrogen Oxides; D009705:Nucleosides; D009942:Organometallic Compounds; D017971:Tin Compounds; C015388:nitrones; C099033:acetonitrile anion; C041694:stannic chloride; D008094:Lithium