부산대학교 도서관

Various HIV protease inhibitors have been developed as promising chemotherapeutic agents for the treatment of AIDS. The importance of hydroxyethylamine isosteres in the this field was well witnessed by antiviral agents such as saquinavir, amprenavir and nelfinavir. In connection of our studies on the development of an improved drug delivery system, we were interested in the synthesis of amprenavir related compounds. Among many reports on the synthesis of this class of inhibitors, we focused on the synthetic scheme that relies on the use of protected aminoalkyl epoxides. On the way to the synthesis of crucial 2(S)-[1(S)-azido-2-phenylethyl]oxirane according to the known procedure we needed to devise a more efficient route to this key intermediate to avoid tedious experimental conditions. Here we wish to report a brief synthesis of oxirane which is more efficient and suitable for preparation on a large scale.