精细与专用化学品
精細與專用化學品
정세여전용화학품
FINE AND SPECIALTY CHEMICALS
2012年
2期
17-19
,共3页
盐酸吉西他滨%S-甘油醛缩丙酮%抗肿瘤药%合成
鹽痠吉西他濱%S-甘油醛縮丙酮%抗腫瘤藥%閤成
염산길서타빈%S-감유철축병동%항종류약%합성
gemcitabine hydrochloride%（S）-glyceraldehyde acetonide%antitumor drug%synthesis
S-甘油醛缩丙酮经Reformasty反应、脱异丙叉基保护、内酯化及双苯甲酰化得到2-脱氧-2,2-二氟-D-赤型-呋喃戊糖-1-酮-3,5-二苯甲酸酯,再经四氢铝锂还原、甲磺酰化、缩合得2-脱氧-2＇,2＇-二氟胞苷-3＇,5＇-二苯甲酸酯,然后经脱保护基,成盐后经丙酮-水体系重结晶分离得盐酸吉西他滨,总收率6.2%。
S-甘油醛縮丙酮經Reformasty反應、脫異丙扠基保護、內酯化及雙苯甲酰化得到2-脫氧-2,2-二氟-D-赤型-呋喃戊糖-1-酮-3,5-二苯甲痠酯,再經四氫鋁鋰還原、甲磺酰化、縮閤得2-脫氧-2＇,2＇-二氟胞苷-3＇,5＇-二苯甲痠酯,然後經脫保護基,成鹽後經丙酮-水體繫重結晶分離得鹽痠吉西他濱,總收率6.2%。
S-감유철축병동경Reformasty반응、탈이병차기보호、내지화급쌍분갑선화득도2-탈양-2,2-이불-D-적형-부남무당-1-동-3,5-이분갑산지,재경사경려리환원、갑광선화、축합득2-탈양-2＇,2＇-이불포감-3＇,5＇-이분갑산지,연후경탈보호기,성염후경병동-수체계중결정분리득염산길서타빈,총수솔6.2%。
3,5-Di-O-benzoyl-2-deoxy-2,2-difluoro-D-ribose was prepared from （S）-glyceraldehyde acetonide via successively Reformasty reaction, deprotect, lactonization and benzoylation. The resulting intermediate was converted to 2 ＇-deoxy-2 ＇ , 2 ＇-difluoro-3 ＇ , 5 ＇-di-O-benzoyl-cytidine via reduction with LiA1H4, methylsulfonation and condensation. Then protect group was removed and the crude product salt was obtained in HC1. After a crystallization in aqueous acetone, the final product was got with an overall yield of 6.2%.
