Chemistry of chiral vitamin B6 analogs. IV. Syntheses of chiral pyridoxal and pyridoxamine analogs having a branched "ansa chain" between 2'- and 5'-positions.
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Racemic 15-formyl-14-hydroxy-5,5-dimethyl-2,8-dithia[9](2,5)pyridinophane (<B>4</B>), an analog of pyridoxal having a branched "ansa chain" between 2′- and 5′-positions, was synthesized from 2,5-bis(chloromethyl)-3-hydroxy-<I>O</I>,<I>O</I>′-isopropylidene-4-pyridinemethanol. Optical resolution of <B>4</B> was achieved <I>via</I> the formation of Schiff base with 3-amino-3-deoxy-1,2:5,6-di-<I>O</I>-isopropylidene-D-glucofranose, giving the levorotary enantiomer of <B>4</B> (<B>4a</B>). Racemic 15-aminomethyl-14-hydroxy-5,5-dimethyl-2,8-dithia[9](2,5)pyridinophane (<B>5</B>), the same type of pyridoxamine analog as <B>4</B>, and its levorotary enantiomer were synthesized from the corresponding <B>4</B> and <B>4a</B>. Both levorotary and dextrorotary enantiomers of <B>5</B> were also obtained by the optical resolution of the racemate <I>via</I> the formation of chiral dibenzoyltartaric acid salts of <B>5</B>.
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- Chemistry of chiral vitamin B6 analogs. IV. Syntheses of chiral pyridoxal and pyridoxamine analogs having a branched "ansa chain" between 2'- and 5'-positions.