Novel Synthesis of (3R,4R)‐4‐Acetoxy‐3‐[1′(R)‐tert‐butyldimethylsilyloxyethyl] Azetidin‐2‐one: A Key Intermediate for Penem and Carbapenem Synthesis

Singh, Santosh K.; Singh, G. B.; Byri, V. K.; Satish, B.; Dhamjewar, Ravi; Gopalan, Began

doi:10.1080/00397910701651300

Synthetic Communications

2008

DOI: 10.1080/00397910701651300

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Novel Synthesis of (3R,4R)‐4‐Acetoxy‐3‐[1′(R)‐tert‐butyldimethylsilyloxyethyl] Azetidin‐2‐one: A Key Intermediate for Penem and Carbapenem Synthesis

Santosh K. Singh¹,

G. B. Singh²,

V. K. Byri³

et al.

Abstract: Diastereoselective synthesis of (3R,4R)-4-acetoxy-3-[1 0 (R)-tert-butyldimethylsilyloxyethyl] azetidin-2-one (AOSA) using (-)-D-2,10-camphorsultam as a key and recyclable chiral auxiliary is described.

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Cited by 9 publications

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ChemInform Abstract: Novel Synthesis of (3R,4R)‐4‐Acetoxy‐3‐[1′(R)‐tert‐butyldimethylsilyloxyethyl] Azetidin‐2‐one: A Key Intermediate for Penem and Carbapenem Synthesis.

Singh¹,

Singh²,

Byri³

et al. 2008

ChemInform

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Antibiotics U 1200Novel Synthesis of (3R,4R)-4-Acetoxy-3-[1'(R)-tert-butyldimethylsilyloxyethyl] Azetidin-2-one: A Key Intermediate for Penem and Carbapenem Synthesis. -2,10-Camphorsultam is used as chiral auxiliary for a novel approach to title compound (XIII), a key intermediate in the industrial-scale synthesis of new-generation β-lactams. The Michael addition to (VII) and the last step to the targeted compound follows known procedures. -(SINGH, S. K.; SINGH, G. B.; BYRI, V. K.; SATISH, B.; DHAMJEWAR*, R.; GOPALAN, B.; Synth. Commun. 38 (2008) 3, 456-464; Matrix Lab. Ltd., Medak Dist, Jinnaram 502 325, India; Eng.) -H. Haber 28-204

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ChemInform Abstract: Novel Synthesis of (3R,4R)‐4‐Acetoxy‐3‐[1′(R)‐tert‐butyldimethylsilyloxyethyl] Azetidin‐2‐one: A Key Intermediate for Penem and Carbapenem Synthesis.

Singh¹,

Singh²,

Byri³

et al. 2008

ChemInform

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show abstract

HDAC and NF-κB mediated cytotoxicity induced by novel N-Chloro β-lactams and benzisoxazole derivatives

Reddy

Suthindhiran

et al. 2016

Chemico-Biological Interactions

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Stereoselective determination of 2-benzamidomethyl-3-oxobutanoate and methyl-2-benzoylamide-3-hydroxybutanoate by chiral high-performance liquid chromatography in biotransformation

Chen

Zheng

Liu

et al. 2015

Journal of Chromatography B

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Novel Synthesis of (3R,4R)‐4‐Acetoxy‐3‐[1′(R)‐tert‐butyldimethylsilyloxyethyl] Azetidin‐2‐one: A Key Intermediate for Penem and Carbapenem Synthesis

Abstract: Diastereoselective synthesis of (3R,4R)-4-acetoxy-3-[1 0 (R)-tert-butyldimethylsilyloxyethyl] azetidin-2-one (AOSA) using (-)-D-2,10-camphorsultam as a key and recyclable chiral auxiliary is described.

Cited by 9 publications

References 19 publications

ChemInform Abstract: Novel Synthesis of (3R,4R)‐4‐Acetoxy‐3‐[1′(R)‐tert‐butyldimethylsilyloxyethyl] Azetidin‐2‐one: A Key Intermediate for Penem and Carbapenem Synthesis.

ChemInform Abstract: Novel Synthesis of (3R,4R)‐4‐Acetoxy‐3‐[1′(R)‐tert‐butyldimethylsilyloxyethyl] Azetidin‐2‐one: A Key Intermediate for Penem and Carbapenem Synthesis.

HDAC and NF-κB mediated cytotoxicity induced by novel N-Chloro β-lactams and benzisoxazole derivatives

Stereoselective determination of 2-benzamidomethyl-3-oxobutanoate and methyl-2-benzoylamide-3-hydroxybutanoate by chiral high-performance liquid chromatography in biotransformation

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