Synthesis of 7-(2,4-dichlorophenyl)-d-erythro-3-hydroxy-5-heptanolide, 6-(2,4-dichlorophenyl)-d-erythro-2,4-dihydroxyhexane-1-sulfonic acid, and 6-(2,4-dichlorophenyl)-d-erythro-2,4-dihydroxyhexylphosphonic acid☆

Add time:09/03/2019    Source:sciencedirect.com

6-(2,4-Dichlorophenyl)-d-erythro-1,2,4-hexanetriol, synthesised from d-glucose, was partially silylated, then reacted with 2-methoxypropene to afford 1-O-tert-butyldimethylsilyl-6-(2,4-dichlorophenyl)-2,4-O-isopropylidene-d-erythro-1,2,4-hexanetriol (17). Desilylation of 17 gave 6-(2,4-dichlorophenyl)-2,4-O-isopropylidene-d-erythro-1,2,4-hexanetriol, which was converted into the 1-tosylate 18 and the 1-bromo derivative 19. Reaction of 18 with potassimum thiolbenzoate gave, after debenzoylation, oxidation, and deprotection, 6-(2,4-dichlorophenyl)-d-erythro-2,4-dihydroxyhexane-1-sulfonic acid (4). Reaction of 18 or 19 with triethyl phosphite gave, after deprotection, 6-(2,4-dichlorophenyl)-d-erythro-2,4-dihydroxyhexylphosphonic acid (5), and reaction of 19 with potassium cyanide gave, after subsequent hydrolysis and deprotection, 7-(2,4-dichlorophenyl)-d-erythro-3-hydroxy-5-heptanolide (3).

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