Stereospecfic Synthesis of Cis-Alkenyl Thioethers of Mercaptolycerol

Mercaptoglycerol 중 cis-alkenyl thioethers의 입체 특이적 합성

Methods were developed to synthesize optically active mercaptoglycerol from optically active isopropylidene glycerols. 1,2-Isopropylideneglycerol was tosylated and the tosyl group displaced with thiolacetate. Base hydrolysis and oxidation gave 1,1'-dithiobis-2,3-isopropylidene-2,3-propanediol. This compound could be used as a source of mercaptoglycerol, or reacted with 1-decenyl lithium to form cis-1-S-dec-1'enyl-2,3-isopropylidene-1-mercapto-2,3-propanediol. The latter is a stereospecific synthetic route to cis-alkenyl thioethers of protected mercaptoglycerol, and it may be useful for the preparation of a thioplasmalogen substrate for plasmalogenase.

광학성체인 isopropylidene glycerols로 부터 mercaptogiycerol을 합성하였다. 1,2-Isopropylideneglycerol을 tosyl화 하고 다시 tosyl group을 thiolacetate로 치환하였다. 염기성 가수분해와 산화에 의해 1,1'-dithiobis-2,3-isopropylidene-2,3-propanediol이 생성되었다. 이 화합물을 mercaptogiycerol 합성을 위해 사용함으로써 1-decenyl lithium으로 cis-S-dec-1'-enyl-2,3-isopropylidene-1-mercapto-2,3-propanediol을 생성하였다. 본 생성물은 plasmalogenase용 thioplasmaloger 기질 조제에 사용된다.