6905-58-4Relevant articles and documents
Lipid analogs of the nodulation factors using the ugi/passerini multicomponent reactions: Preliminary studies on the carbohydrate monomer
Grenouillat, Nathalie,Vauzeilles, Boris,Beau, Jean-Marie
, p. 891 - 901 (2007)
Treament of 1,3,4,6-tetra-O-acetyl-2-deoxy-2-isocyano-β-D-gluco-pyranose and the corresponding β-allyl glycoside with octanal and acetic acid provide the Passerini products in excellent yields whereas the corresponding Ugi transformation in the presence of i-propylamine proceeded with much lower efficiency. This work represents a preliminary investigation on a project directed towards the modification of the lipid moiety of the nodulation factors.
Reactions of Relevance to the Chemistry of Aminoglycoside Antibiotics. Part 14. A Useful Radical-deamination Reaction
Barton, Derek H. R.,Bringmann, Gerhard,Lamotte, Genevieve,Motherwell, William B.,Motherwell, Robyn S. Hay,Porter, Alexander E. A.
, p. 2657 - 2664 (2007/10/02)
Primary, secondary, and tertiary aliphatic or alicyclic isocyanides are smoothly reduced under radical conditions using tri-n-butylstannane to the corresponding hydrocarbons.The relative ease of reduction is tertiary > secondary > primary.Aromatic isocyanides are not reduced under these conditions.The reduction of isothiocyanates (or isoselenocyanates) by tri-n-butylstannanae also affords hydrocarbons, but here the isocyanides have been shown to be intermediates.The reduction of a compound with isocyanide and xanthate functions in a 1,2-relationship gives a smooth radical fragmentation to furnish an olefin.An efficient synthesis of 2-deoxy-D-glucose starting with glucosamine is described.
