Synthesis of 2-(Heteroarylthiomethyl)-1β-methylcarbapenem via Propargylation of 4-Acetoxy-2-azetidinone with 3-Methyl-1-tributylstannylallene

The key intermediate in the synthesis of 1β-methylcarbapenem, (3S, 4R)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1S)-1-methyl-2-propynyl]-2-azetidinone (5β), was prepared by propargylation of (3R, 4R)-4-acetoxy-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone (3) with 3-methyl-1-tri...

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Veröffentlicht in:	Chemical & pharmaceutical bulletin 1989/09/25, Vol.37(9), pp.2338-2343
Hauptverfasser:	HARUTA, Jun-ichi, NISHI, Koichi, KIKUCHI, Kazumi, MATSUDA, Satoshi, TAMURA, Yasumitsu, KITA, Yasuyuki
Format:	Artikel
Sprache:	eng
Schlagworte:	2-(heteroarylthiomethyl)-1β-mehylcarbapenem 3-methyl-1-tributylstannylallene 4-acetoxy-2-azetidinone 4[(1S)-1-methyl-2-propynyl]-2-azetidinone Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Organic chemistry Preparations and properties propargylation
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Zusammenfassung:	The key intermediate in the synthesis of 1β-methylcarbapenem, (3S, 4R)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1S)-1-methyl-2-propynyl]-2-azetidinone (5β), was prepared by propargylation of (3R, 4R)-4-acetoxy-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone (3) with 3-methyl-1-tributylstannylallene (4) in the presence of a Lewis acid and successfully converted to a novel 2-(heteroarylthiomethyl)-1β-methylcarbapenem (2).
ISSN:	0009-2363 1347-5223
DOI:	10.1248/cpb.37.2338