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Volumn 38, Issue 3, 2008, Pages 456-464

Novel synthesis of (3R,4R)-4-acetoxy-3-[1′(R)-tert- butyldimethylsilyloxyethyl] azetidin-2-one: A key intermediate for penem and carbapenem synthesis

Author keywords

lactam; Camphorsultam; Diastereoselective; Silylation

Indexed keywords

4 ACETOXY 3 [1' (R) TERT BUTYLDIMETHYLSILYLOXYETHYL] AXETIDIN 2 ONE; AZETIDINONE DERIVATIVE; CAMPHOR DERIVATIVE; CARBAPENEM; PENEM DERIVATIVE; UNCLASSIFIED DRUG;

EID: 38649098175     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701651300     Document Type: Article
Times cited : (11)

References (28)
  • 1
    • 38649099934 scopus 로고    scopus 로고
    • Gopalan, B, Ravi, D, Singh, S. K. A novel synthesis of (3R,4R)-4-acetoxy-3-[1′(R)-tert-butyldimethylsilyloxyethyl]azetidin-2-one: A key intermediate for penem and carbapenem synthesis. Indian Patent Application No. 175/CHE/2007, Jan. 29, 2007
    • Gopalan, B.; Ravi, D.; Singh, S. K. A novel synthesis of (3R,4R)-4-acetoxy-3-[1′(R)-tert-butyldimethylsilyloxyethyl]azetidin-2-one: A key intermediate for penem and carbapenem synthesis. Indian Patent Application No. 175/CHE/2007, Jan. 29, 2007.
  • 2
    • 0035109271 scopus 로고    scopus 로고
    • The structural aspects of carbapenem antibiotics
    • (a) Sunagawa, M.; Sasaki, A. The structural aspects of carbapenem antibiotics. Heterocycles 2001, 54, 497-528;
    • (2001) Heterocycles , vol.54 , pp. 497-528
    • Sunagawa, M.1    Sasaki, A.2
  • 5
    • 0025279314 scopus 로고
    • A novel carbapenem antibiotic, SM-7338 structure-activity relationships
    • (a) Sunagawa, M.; Matsumura, H.; Inoue, T. A novel carbapenem antibiotic, SM-7338 structure-activity relationships. J. Antibiotic. 1990, 43, 519-532;
    • (1990) J. Antibiotic , vol.43 , pp. 519-532
    • Sunagawa, M.1    Matsumura, H.2    Inoue, T.3
  • 6
    • 0032563831 scopus 로고    scopus 로고
    • A highly refined version of the α-keto ester based carbapenem synthesis: The total synthesis of meropenem
    • (b) Prasad, A. S.; Vlahos, N.; Fabio, P.; Feigelson, G. B. A highly refined version of the α-keto ester based carbapenem synthesis: The total synthesis of meropenem. Tetrahedron Lett. 1998, 39, 7035-7038.
    • (1998) Tetrahedron Lett , vol.39 , pp. 7035-7038
    • Prasad, A.S.1    Vlahos, N.2    Fabio, P.3    Feigelson, G.B.4
  • 8
    • 33746913557 scopus 로고    scopus 로고
    • Novel synthetic route of a pivotal intermediate for the synthesis of 1β-methylcarbapenem antibiotics
    • (b) Yu, Y.; Zhou, W.; Zhang, J.; Zhang, M.; Xu, D.; Tang, Y.; Li, B.; Yu, X. Novel synthetic route of a pivotal intermediate for the synthesis of 1β-methylcarbapenem antibiotics. Org. Process Res. Dev. 2006, 10, 829-832.
    • (2006) Org. Process Res. Dev , vol.10 , pp. 829-832
    • Yu, Y.1    Zhou, W.2    Zhang, J.3    Zhang, M.4    Xu, D.5    Tang, Y.6    Li, B.7    Yu, X.8
  • 12
    • 38649105085 scopus 로고
    • Process for preparing optically active 3-hydroxybutanoic acid
    • US Patent 4981992, Jan. 1
    • (c) Sayo, N.; Saito, T.; Okeda, Y.; Nagashima, H.; Kumobayashi, H. Process for preparing optically active 3-hydroxybutanoic acid. US Patent 4981992, Jan. 1, 1991;
    • (1991)
    • Sayo, N.1    Saito, T.2    Okeda, Y.3    Nagashima, H.4    Kumobayashi, H.5
  • 13
    • 38649123940 scopus 로고
    • Ruthenium catalyzed process for preparing 4-acetoxyazetidinones
    • US Patent 5081239, Jan. 14
    • (d) Saito, T.; Kumobayashi, H. Ruthenium catalyzed process for preparing 4-acetoxyazetidinones. US Patent 5081239, Jan. 14, 1992;
    • (1992)
    • Saito, T.1    Kumobayashi, H.2
  • 14
    • 38649090632 scopus 로고
    • Substituted acetoxyazetidinone derivatives and process for preparing 4-acetoxyazetidinone derivatives
    • US Patent 5288862, Feb. 22
    • (e) Saito, T.; Kumobayashi, H.; Murahashi, S. Substituted acetoxyazetidinone derivatives and process for preparing 4-acetoxyazetidinone derivatives. US Patent 5288862, Feb. 22, 1994;
    • (1994)
    • Saito, T.1    Kumobayashi, H.2    Murahashi, S.3
  • 15
    • 38649091622 scopus 로고
    • Acetoxylation process for producing 4-acetoxyazetidinones with osmium catalyst
    • US Patent 5191076, Mar. 2
    • (f) Saito, T.; Kumobayashi, H.; Murahashi, S. Acetoxylation process for producing 4-acetoxyazetidinones with osmium catalyst. US Patent 5191076, Mar. 2, 1993;
    • (1993)
    • Saito, T.1    Kumobayashi, H.2    Murahashi, S.3
  • 16
    • 0025855917 scopus 로고
    • A facile conversion of the phenylthio group to acetoxy by copper reagents for a practical synthesis of 4-acetoxyazetidin-2-one derivatives from (R)-butane-1,3-diol
    • (g) Nakatsuka, T.; Iwata, H.; Tanaka, R.; Imajo, S.; Ishiguro, M. A facile conversion of the phenylthio group to acetoxy by copper reagents for a practical synthesis of 4-acetoxyazetidin-2-one derivatives from (R)-butane-1,3-diol. J. Chem. Soc., Chem. Commun. 1991, 662-664;
    • (1991) J. Chem. Soc., Chem. Commun , pp. 662-664
    • Nakatsuka, T.1    Iwata, H.2    Tanaka, R.3    Imajo, S.4    Ishiguro, M.5
  • 17
    • 38649095151 scopus 로고
    • Process for the preparation of 4-acetoxy-2-azetidinone derivatives
    • US Patent 5026844, Jun. 25
    • (h) Ishiguro, M.; Iwata, H.; Nakatsuka, T.; Yamada, Y. Process for the preparation of 4-acetoxy-2-azetidinone derivatives. US Patent 5026844, Jun. 25, 1991.
    • (1991)
    • Ishiguro, M.1    Iwata, H.2    Nakatsuka, T.3    Yamada, Y.4
  • 18
    • 0030028910 scopus 로고    scopus 로고
    • Preparation of two pivotal intermediates for the synthesis of 1-β-methyl carbapenem antibiotics: A review
    • and references cited therein;
    • (a) Berks, A. H. Preparation of two pivotal intermediates for the synthesis of 1-β-methyl carbapenem antibiotics: A review. Tetrahedron 1996, 52, 331-375 and references cited therein;
    • (1996) Tetrahedron , vol.52 , pp. 331-375
    • Berks, A.H.1
  • 19
    • 15844371368 scopus 로고    scopus 로고
    • A facile synthesis of the key intermediate for penems, carbapenems, and related β-lactam antibiotics
    • (b) Seki, M.; Yamanaka, T.; Miyake, T.; Ohmizu, H. A facile synthesis of the key intermediate for penems, carbapenems, and related β-lactam antibiotics. Tetrahedron Lett. 1996, 37, 5565-5568;
    • (1996) Tetrahedron Lett , vol.37 , pp. 5565-5568
    • Seki, M.1    Yamanaka, T.2    Miyake, T.3    Ohmizu, H.4
  • 20
    • 0031371377 scopus 로고    scopus 로고
    • Stereocontrolled synthesis of 4-acetoxy-2-azetidinone via double azetidinone ring formation: A useful precursor of carbapenem and penem antibiotics
    • (c) Kwon, H.; Lee, M.; Lee, I.; Lee, S.; Yoon, T.; Hwang, T. Stereocontrolled synthesis of 4-acetoxy-2-azetidinone via double azetidinone ring formation: A useful precursor of carbapenem and penem antibiotics. Bull. Korean Chem. Soc. 1997, 18, 475-478;
    • (1997) Bull. Korean Chem. Soc , vol.18 , pp. 475-478
    • Kwon, H.1    Lee, M.2    Lee, I.3    Lee, S.4    Yoon, T.5    Hwang, T.6
  • 21
    • 0032532575 scopus 로고    scopus 로고
    • A practical synthesis of a key intermediate for the production of β-lactam antibiotics
    • (d) Cainelli, G.; Galletti, P.; Giacomini, D. A practical synthesis of a key intermediate for the production of β-lactam antibiotics. Tetrahedron Lett. 1998, 39, 7779-7782;
    • (1998) Tetrahedron Lett , vol.39 , pp. 7779-7782
    • Cainelli, G.1    Galletti, P.2    Giacomini, D.3
  • 22
    • 0031906061 scopus 로고    scopus 로고
    • A short, stereoselective synthesis of (3R,4R)-4-acetoxy-3-[(R)-1′((t- butyldimethylsilyl)oxy)ethyl]-2-azetidinone, key intermediate for the preparation of carbapenem antibiotics
    • (e) Franco, C.; Rita, A.; Mauro, C.; Laura, P.; Alcide, P.; Bruno, T. A short, stereoselective synthesis of (3R,4R)-4-acetoxy-3-[(R)-1′((t- butyldimethylsilyl)oxy)ethyl]-2-azetidinone, key intermediate for the preparation of carbapenem antibiotics. Chirality 1998, 10, 91-94;
    • (1998) Chirality , vol.10 , pp. 91-94
    • Franco, C.1    Rita, A.2    Mauro, C.3    Laura, P.4    Alcide, P.5    Bruno, T.6
  • 23
    • 38649114955 scopus 로고    scopus 로고
    • Synthesis of (3R,4R)-4-acetoxy-3- [(R)-1′-(t-butyldimethylsilyloxy) ethyl]-2-azetidinone
    • f
    • (f ) Wang, Y.; Liu, J.; Qu, C.; Hu, L. Synthesis of (3R,4R)-4-acetoxy-3- [(R)-1′-(t-butyldimethylsilyloxy) ethyl]-2-azetidinone. Chem. Abstr. 1998, 129, 81602e.
    • (1998) Chem. Abstr , vol.129
    • Wang, Y.1    Liu, J.2    Qu, C.3    Hu, L.4
  • 24
    • 0026334232 scopus 로고
    • Asymmetric silyl nitronate cycloadditions with borane-10,2-sultam derivatives
    • (a) Kim, B. H.; Lee, J. Y. Asymmetric silyl nitronate cycloadditions with borane-10,2-sultam derivatives. Tetrahedron: Asymmetry 1991, 2, 1359-1370;
    • (1991) Tetrahedron: Asymmetry , vol.2 , pp. 1359-1370
    • Kim, B.H.1    Lee, J.Y.2
  • 25
    • 0001071065 scopus 로고
    • Lithium-initiated imide formation: A simple method for N-acylation of 2-oxazolidinones and bornane-2,10-sultam
    • (b) Ho, G.; Mathre, D. J. Lithium-initiated imide formation: A simple method for N-acylation of 2-oxazolidinones and bornane-2,10-sultam. J. Org. Chem. 1995, 60, 2271-2273.
    • (1995) J. Org. Chem , vol.60 , pp. 2271-2273
    • Ho, G.1    Mathre, D.J.2
  • 26
  • 27
    • 0028823006 scopus 로고
    • A simple route to α-substituted- β-amino ester precursors of carbapenem antibiotics
    • (a) Perlmutter, P.; Tabone, M. A simple route to α-substituted- β-amino ester precursors of carbapenem antibiotics. J. Org. Chem. 1995, 60, 6515-6522;
    • (1995) J. Org. Chem , vol.60 , pp. 6515-6522
    • Perlmutter, P.1    Tabone, M.2
  • 28
    • 0000057857 scopus 로고
    • Diastereoselection in the nucleophilic conjugate addition of amines to 2-hydroxyalkylpropenoates
    • (b) Perlmutter, P.; Tabone, M. Diastereoselection in the nucleophilic conjugate addition of amines to 2-hydroxyalkylpropenoates. Tetrahedron Lett. 1988, 29, 949-952.
    • (1988) Tetrahedron Lett , vol.29 , pp. 949-952
    • Perlmutter, P.1    Tabone, M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.