陈芬儿, 冯秀梅, 张珩, 万江陵, 别立亮, 管春生, 杨建设, 凌秀红. d-生物素的立体专一性全合成研究J. 药学学报, 1995, 30(11): 824-830.
引用本文: 陈芬儿, 冯秀梅, 张珩, 万江陵, 别立亮, 管春生, 杨建设, 凌秀红. d-生物素的立体专一性全合成研究J. 药学学报, 1995, 30(11): 824-830.
FE Chen, XM Feng, H Zhang, JL Wan, LL Bie, CS Guan, JS Yang , XH Ling, . STUDIES ON STEREOSPECIFIC TOTAL SYNTHESIS OF d-BIOTINJ. Acta Pharmaceutica Sinica, 1995, 30(11): 824-830.
Citation: FE Chen, XM Feng, H Zhang, JL Wan, LL Bie, CS Guan, JS Yang , XH Ling, . STUDIES ON STEREOSPECIFIC TOTAL SYNTHESIS OF d-BIOTINJ. Acta Pharmaceutica Sinica, 1995, 30(11): 824-830.

d-生物素的立体专一性全合成研究

STUDIES ON STEREOSPECIFIC TOTAL SYNTHESIS OF d-BIOTIN

  • 摘要: 对confaione的d-生物素(1)全合成进行了改进,从半胱氨酸计算,总收率3.7%。5与4-溴代三苯膦丁酸甲酯进行Wittig-Schlosser缩合反应可立体专一性地转化成反式-烯(6)。以叠氮三甲基硅烷代替叠氮化锂亲核进攻9分子中C3-溴原子,可显著地提高顺式-叠氮内酰胺10的收率。

     

    Abstract: A modified stereospecific total synthesis of d-biotin from L-(+)-cysteine based on Confalone’ s method was described, Witting-Schlosser olefination of the aldehyde(5) with Witting reagent derived from carbomethoxypropyl-triphenylphosphonium bromide ,after acidic work-up,furnished transolefin(6 ) stereospecifically in 72% yield.Treatment of the bromolactam(9) with azidotrimethylsilane instead of lithium azide via SN2 nucleophilic substitution increased the yield of cis azido lactam(10).The overall yield of d-biotin was 3.7%from cysteine.

     

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