New alpha-amino-nitrile derivatives of saccharide, itol or nucleoside substrate compounds, used as intermediates for e.g. aminoacids, heterocycles or antiviral drugs

摘要

alpha -Aminonitriles (I) are new. alpha -Aminonitriles of formula (I) are new. Sub = optionally protected, cyclic or acyclic saccharide or itol derivative (e.g. a hexose, pentose, hexitol, pentitol, tetritol or glycerol residue, preferably the residue of glucose, galactose, mannose, fructose, ribose, glucitol, galactitol, mannitol, xylitol, erythritol or glycerol); or a nucleoside residue (e.g. a thymidine, uridine, guanidine, cytosine or adenine residue); R1, R2 = H, OH, NH2, NHR, NRR', Me, Et, alkyl, aminoalkyl, allyl, benzyl or alkylene; haloalkyl or haloalkylene (where halo is preferably F or Cl); COR, CHRCOOH, C(O)SR or COOR; optionally protected, cyclic or acyclic mono-, di-, tri- or polysaccharide or itol derivative (e.g. a hexose, pentose, hexitol, pentitol, tetritol or glycerol residue, preferably the residue of glucose, galactose, mannose, fructose, ribose, glucitol, galactitol, mannitol, xylitol, erythritol or glycerol); or nucleoside residue (e.g. a thymidine, uridine, guanidine, cytosine or adenine residue); R = H, OH, Me, Et, alkyl, aminoalkyl or benzyl; R' is not defined. An Independent claim is included for the preparation of (I) comprising: (a) preparing an imine or iminium derivative from a saccharide, itol or nucleoside substrate compound (activated as a ketone or aldehyde derivative) and an amine; (b) condensing with cyanide ion; and (c) optionally deprotecting. The method optionally includes further stages for the conversion of (I).