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化学学报
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化学学报 ›› 2001, Vol. 59 ›› Issue (2): 279-283. 上一篇    下一篇

研究论文

光学活性3-(1'-羟基乙基)-4- 乙酰氧基-β-内酰胺的立体选择 性合成

胡键;吴彤;李恒光;谢如刚;甘亚;吕丁   

  1. 四川大学化学系.成都(610064);四川抗菌素工业研究所
  • 发布日期:2001-02-15

Asymmetric synthesis of the optically active 3-(1'-hydroxyethyl)- 4- acetoxy-β-lactam

Hu Jian;Wu Tong;Li Hengguang;Xie Rugang;Gan Ya;Lu Ding   

  1. Sichuan Univ, Dept Chem.Chengdu(610064)
  • Published:2001-02-15

PDF

420

被引次数

16

(1'R,3R,4R)-N-取代-3-(1'-羟基乙基)-4-乙酰氧基-β-内酰胺(3)是合成青霉烯和碳青霉烯类β-内酰胺抗生素的关键中间体。以廉价的L-抗坏血酸为原料，制得S-缩异丙氧叉甘油醛(5)，与胺反应定量转变成相应的手性亚胺(6a～6d)，6与双烯酮[2+2]环加成反应，高立体选择性地合成3(S)-乙酰基-β-内酰胺(8a～8d)，其非对映体过量由类似反庆的80%提高到接近100%。8a经四步反应得到目标化合物3a。

关键词: 光学活性, 乙酰氧基, 立体选择性, 环加成反应, 抗坏血酸, β内酰胺, 抗生素

(1'R, 3R, 4R)-N-substituted -3-(1'-hydroxyethyl)-4-acetoxy-β- lactams(3), a key intermediate for synthesis of the bapenem and carbapenem, has been efficiently synthesized using inexpensive L - ascorbic acid (4) as the chiral reagent. (S) - glyceraldehyde acetonide (5) was prepared conveniently by three steps from 4, and condensed with amines to give the chiral imines (6). The [2+2]-cycloaddition of diketene with the chiral imines(6) underwent in a highly stereoselective manner to give a series of 3(S)-acetyl-β-lactams(8). The target compound 3a was then obtained through further reactions from 8a.

Key words: ACETOXY GROUP, STEREOSELECTIVITY, CYCLOADDITION REACTION, ASCORBIC ACID, BETA LACTAM, ANTIBIOTICS

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