Carbohydrate Research p. 99 - 112 (1986)
Update date:2022-09-26
Topics:
Aparicio, F. J. Lopez
Gonzalez, F. Santoyo
Mendoza, P. Garcia
Mateo, F. Hernandez
Martinez, J. A. Dominguez
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.
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