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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 13, Number 3
BKCSDE 13(3)
March 20, 1992 

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
Bong Young Chung*, Cha Soo Nah, Jin Yeon Kim, Hakjune Rhee, Young Chul Cha
A new monocyclic β-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-α -(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 β -lactam compound 3 were, however, found to be quite low compared to cefotaxime.
311 - 314
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