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Total Synthesis of Sodium (3R,4S)-3-[2-(2-Aminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-4-methoxymethyl-2-azetidinone-1-sulfonate from L-Aspartic Acid
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  • Total Synthesis of Sodium (3R,4S)-3-[2-(2-Aminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-4-methoxymethyl-2-azetidinone-1-sulfonate from L-Aspartic Acid
  • Total Synthesis of Sodium (3R,4S)-3-[2-(2-Aminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-4-methoxymethyl-2-azetidinone-1-sulfonate from L-Aspartic Acid
저자명
Chung. Bong Young,Nah. Cha Soo,Kim. Jin Yeon,Rhee. Hakjune,Cha. Young Chul
간행물명
Bulletin of the Korean Chemical Society
권/호정보
1992년|13권 3호|pp.311-314 (4 pages)
발행정보
대한화학회
파일정보
정기간행물|ENG|
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이 논문은 한국과학기술정보연구원과 논문 연계를 통해 무료로 제공되는 원문입니다.
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기타언어초록

A new monocyclic ${eta}-lactam$ analogue, sodium (3R,4S)-3-[2-(2-aminothiazol-4-yl)-(Z)-2-methoxyi minoacetamido]-4-methoxymethyl-2-azetidinone-1- sulfonate (3) was synthesized from L-aspartic acid. Starting from L-aspartic acid, (S)-1-benzyl-4-benzyloxycarbonyl-2-azetidinone (7) was synthesized in four steps by following the established procedures and converted into (3R,4S)-3-amino-1-t-butyldimethylsilyl-4-methoxym ethyl-2-azetidinone (13) in six steps. Acylation of the amino group of 13 with $2-amino-{alpha}$ -(methoxyimino)-4-thiazoleacetic acid, desilylation, and sulfonation with sulfur trioxide-pyridine complex followed by ion exchange afforded sodium (3R,4S)-3-[2-(2-aminothiazol-4-yl)-(Z)-2-methoxyi minoacetamido]-4-methoxymethyl-2-azetidinone-1- sulfonate (3). Antibacterial activities of this ${eta}$ -lactam compound 3 were, however, found to be quite low compared to cefotaxime.