Jeong L S, Lee J E, Kim H O, Chun M W
College of Pharmacy, Ewha Womans University, Seoul, Korea.
Arch Pharm Res. 1998 Jun;21(3):338-43. doi: 10.1007/BF02975298.
2'-Fluorohexopyranosyl nucleosides 1a and 1b which contained a bioisosteric double bond and a fluorine were synthesized in 12 steps, starting from D-galactose. During diethylaminosulfur trifluoride (DAST) fluorination, retention of stereochemistry was observed through the participation of methoxy or chloro group at the 6-position of the purine base. The final nucleosides 1a and 1b were found to be inactive against HIV-1 and HSV-1,2.
以D-半乳糖为起始原料，经12步反应合成了含有生物电子等排双键和氟的2'-氟己吡喃糖基核苷1a和1b。在二乙氨基三氟化硫（DAST）氟化过程中，通过嘌呤碱6位甲氧基或氯的参与观察到立体化学的保持。发现最终的核苷1a和1b对HIV-1和HSV-1、2无活性。
