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有机化学
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有机化学 ›› 1989, Vol. 9 ›› Issue (1): 69-72. 上一篇    下一篇

研究论文

在青霉素上立体选择引入6α-甲(烷)氧基的新方法

钟伊利;李润荪;雷兴翰   

  1. 国家医药管理局上海医药工业研究院
  • 发布日期:1989-02-25

A novel stereoselective method for the introduction of a methoxy (alkoxy) group into the 6 α-position of penicillins

ZHONG YILI;LI RUNSUN;LEI XINGHAN   

  • Published:1989-02-25

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本文报导了在青霉素上立体选择引入6α-甲(烷)氧基的新方法. 苄青雷素钾盐经酯化, 亚硝化, 重氮化, 还原而制得的6-腙青雷素与芳醛在对甲苯磺酸(PTS)的催化下, 以低级醇为溶剂, 在室温反应1-2h, 即于生成连氮侧链的同时, 将相应的烷氧基引入到6α位上, 得6α-烷氧基-6β-取代腙青霉素.

关键词: 青霉素, 甲氧基, 甲氧基, 立体选择性, 内酰胺, 加成反应, 头孢霉素, 烷氧化反应

6a-Alkoxy-6b-hydrazonopenicilins I (R = PhCH2, Me3CCO2CH2, CH2:CHCH2; R1 = Me, Et, Pr, Me2CH, MeOCH2CH2; X = O, S, vinylene) were prepared by reaction of 6-hydrazonopenicillin with aromatic aldehydes II (X = O, S, vinylene) in R1OH in the presence of protic acid at room temperature to form 6-arom. substituted azinopenicillins. Nucleophilic attack of R1OH on C-6 of the latter compounds, due to activation by the nitro group, gave I.

Key words: PENICILLIN, METHOXY GROUP, METHOXY GROUP, STEREOSELECTIVITY, LACTAM, ADDITION REACTION, CEPHALOSPORINS

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