Abstract
3,7,8-Trideoxy-8-phosphono- d- arabino-octulosonic acid and 7,8-dedeoxy-8-phosphobno-D- gluco-octulosonic acid were synthesised in six step from known, protected derivatives of 2-deoxy- d- arabino-hexose and d-glucose. The protected 6- aldehydo-hexadialdoses were condensed with tetraethyl methylenediphosphonate, and hydrolysis of vinylphosphonate was effected indirectly by transesterification with bromotrimethylsilane. Cyanide addition to deprotected heptose phosphonates was followed by chlorate-vanadate oxidation to octulosonic acid derivatives. The corresponding 3,7-dideoxy-7-phosphono- d- arabino-heptulosonic acid and 7-deoxy-7-phosphono- d- gluco-heptulosonic acid were obtained by reaction of 6-bromo-6-deoxyhexoses with triethyl phosphite, followed by treatment with bromotrimethylsilane, hydrolysis with water, cyanide homologation, and chlorate-vanadate oxidation. All four, final phosphono compounds are competitive inhibitors of 3-dehydroquinate syntyhetase.
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