Stereocontrolled, straightforward synthesis of 3-substituted methyl 7α-methoxy-1-oxacephems

Yoshioka, M.; Tsuji, Teruji; Uyeo, Shojiro; Yamamoto, Sachiko; Aoki, Tsutomu; Nishitani, Yasuhiro; Mori, Suguru; Satoh, Hisao; Hamada, Y.; Ishitobi, Hiroyuki; Nagata, Wataru

doi:10.1016/s0040-4039(01)85470-8

Cited by 42 publications

(2 citation statements)

References 7 publications

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“…Synthetic routes to the oxadethiacephems have been investigated fairly extensively (194,195) and in all the routes published the key step is the stereocontrolled introduction of the ring oxygen function. The synthesis of moxalactam 48, depicted in Figure 10, efficiently retains all the carbons of its starting material, 6-aminopenicillanic acid [551-16-6] (6-APA) 10, C 8 H 12 N 2 O 2 S (194)(195)(196).…”

Section: Synthetic Strategymentioning

confidence: 99%

Cephalosporins

Roberts¹

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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CEPHALOSPORINSThe cephalosporins, a subgroup of β-lactam antibiotics, consist of a 4-membered lactam ring fused through the nitrogen and the adjacent tetrahedral carbon atom to a second heterocycle forming a 6-membered dihydrothiazine ring. Other structural features common to all the cephalosporins are a carboxyl group on the dihydrothiazine ring on the carbon next to the ring nitrogen and a functionalized amino group on C-7, the carbon of the β-lactam ring opposite the nitrogen. These features are evidenced in 7-aminocephalosporanic acid [957-68-6] (7-ACA), C 10 H 12 N 2 O 5 S 1. Cephalosporins, like all β-lactam antibiotics, exert their antibacterial effect by interfering with the synthesis of the bacterial cell wall. These antibiotics tend to be "irreversible" inhibitors of cell wall biosynthesis and they are usually bactericidal at concentrations close to their bacteriostatic levels. Cephalosporins are widely used for treating bacterial infections. They are highly effective antibiotics and have low toxicity.

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Section: Synthetic Strategymentioning

confidence: 99%

Cephalosporins

Roberts¹

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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“…A feasible industrial route by which to synthesize 1-oxacephem 8 in good yield starting from commercially available 6-aminopenicillanic acid (6-APA) ( Figure 2) was reported by Nagata of the Shionogi company [10,11]. In this sophisticated method designed to retain all the carbon atoms, preparing epioxazolinoazetidinones having an unconjugated ester moiety at the β-lactam nitrogen was a breakthrough.…”

Section: Introductionmentioning

confidence: 99%

(1R,5S)-6-(4-Methyl-2-oxo-2,5-dihydrofuran-3-yl)-3-phenyl-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-en-7-one

Pham

Tippin

et al. 2018

Molbank

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Efficient large-scale and feasible industrial synthesis of the 1-oxacephem core structure from 6-aminopenicillanic acid (6-APA) has been reported for several decades. Via the industrial synthesis route, a byproduct (compound 9) containing a butenolide unit was purified and characterized by NMR and HRMS in this work. It is worth noting that compound 9 is an entirely new compound. Additionally, a plausible mechanism and effects on the formation of 9 by different Lewis acids were proposed. The discovery of compound 9 could improve the purity of this feasible industrial synthesis and provide considerable cost savings.

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Copper(I) Oxide

Tückmantel¹

2001

Encyclopedia of Reagents for Organic Synthesis

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Stereocontrolled, straightforward synthesis of 3-substituted methyl 7α-methoxy-1-oxacephems

Cited by 42 publications

References 7 publications

Cephalosporins

Cephalosporins

(1R,5S)-6-(4-Methyl-2-oxo-2,5-dihydrofuran-3-yl)-3-phenyl-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-en-7-one

Copper(I) Oxide

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