REACTION OF 3-HETERO-1,5-DIALDEHYDES WITH tert-BUTYL CYANOACETATE

Article abstract of DOI:10.1016/S0008-6215(00)90291-X

The reaction of thiodiglycolaldehyde and diglycolaldehyde with tert-butyl cyanoacetate yields derivatives of tetrahydrothiopyran and tetrahydropyran, respectively.Similar reactions of diglycolaldehyde derivatives having a furan nucleus at the α-position yield D-xylo (major) and L-arabino (minor) C-pyranosyl derivatives.Starting from α-(S)-methoxy-α'-(R)-hydroxymethyldiglycolaldehyde, D-gluco and D-manno glycosides were obtained, the relative proportions of which depended on the time of reaction.In addition to the 1:1 addition products, minor products corresponding to 1:2 (dialdehyde: active methylene compound) addition were isolated.