Chem. J. Chinese Universities ›› 1987, Vol. 8 ›› Issue (7): 620.
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Nie Xinyong, Wang Qian, Li Yulin, Pan Xinfu
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Abstract: The (2R,3R) -dimethyl tartrate acetonide(1) was reacted with p-benzyloxy-benzyl bromide(2) at-78℃ in the presence of LDAto convert successfully(1) to dimethyl(2R,3R)-2-benzyloxybenzyl-tartrate acetonide (3). The dimethyl (2R, 3R)-2-benzyloxybenzyl-tartrate acetonide (3) was treated with CH3ONa and the major product was the 81% enantiomerically pure erythro-isomer (5). The benzyl and acetonide groups of dimethyl (2R,3S)-2-benzyloxybenzyl tartrate acetonide (5) and dimethyl (2R,3R)-2-benzyloxybenzyl tartrate acetonite (3) were removed, respectively, by treating with CH3CO2H-HCl-H,O(2:1:1) for 1.5 hrs., and hydrolyzing with 0.5N NaOH. The piscidic acid (8) and its epimer (7) were obtained successfully.
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Nie Xinyong, Wang Qian, Li Yulin, Pan Xinfu . Synthesis of Piscidic Acid and Its Epimer[J]. Chem. J. Chinese Universities, 1987, 8(7): 620.
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