Reaction of 3-hetero-1,5-dialdehydes with tert-Butyl cyanoacetate (cas 1116-98-9)☆

Add time:09/09/2019    Source:sciencedirect.com

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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