A FACILE CONVERSION OF THE PHENYLTHIO GROUP TO ACETOXY BY COPPER REAGENTS FOR A PRACTICAL SYNTHESIS OF 4-ACETOXYAZETIDIN-2-ONE DERIVATIVES FROM (R)-BUTANE-1,3-DIOL

被引：52

作者：

NAKATSUKA, T ^{[1
]}

IWATA, H ^{[1
]}

TANAKA, R ^{[1
]}

IMAJO, S ^{[1
]}

ISHIGURO, M ^{[1
]}

机构：

[1] SUNTORY INST BIOMED RES,SHIMAMOTO,OSAKA 618,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1991年 / 09期

关键词：

D O I：

10.1039/c39910000662

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(3S,4R,1'R)-4-Acetoxy-3-(1'-tert-butyldimethylsilyloxyethyl)-azetidin-2-one 8, an important intermediate for the synthesis of penem and carbapenem antibiotics, was synthesized from (R)-butane-1,3-diol 1, using chlorosulphonyl isocyanate for the formation of beta-lactam ring in which a significant solvent effect on the ratio of diastereoisomers 6a and 6b was observed; copper(II) acetate rather than the poisonous mercury(II) acetate was used to convert the phenylthio group of compound 6a to acetoxy.

引用

页码：662 / 664

页数：3

共 19 条

[1]

AFONSO A, 1985, SPEC PUBL ROYAL SOC, V52, P266

[2] THE PREPARATION OF THE 1ST ALPHA-VINYLIDENE-BETA-LACTAMS [J].