메뉴 건너뛰기




Volumn 33, Issue 13, 2003, Pages 2275-2283

A new way to tert-Butyl [(4R,6R)-6-aminoethyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate, a key intermediate of atorvastatin synthesis

Author keywords

Atorvastatin; Henry reaction; Swern oxidation; Synthesis

Indexed keywords

ACETIC ACID DERIVATIVE; ATORVASTATIN; HYDROXYMETHYLGLUTARYL COENZYME A REDUCTASE INHIBITOR; NITRO DERIVATIVE; NITROALDOL; NITROMETHANE; SODIUM BOROHYDRIDE; TERT BUTYL(2,2 DIMETHYL 6 NITROETHYL 1,3 DIOXAN 4 YL)ACETATE; TERT BUTYL(6 AMINOETHYL 2,2 DIMETHYL 1,3 DIOXAN 4 YL)ACETATE; TERT BUTYL(6 FORMYL 2,2 DIMETHYL 1,3 DIOXAN 4 YL)ACETATE; UNCLASSIFIED DRUG;

EID: 17944402728     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120021507     Document Type: Article
Times cited : (25)

References (19)
  • 2
    • 0026559054 scopus 로고
    • The synthesis of (4R-cis)-1, 1-dimethylethyl-6-cyanomethyl-2, 2-dimethyl-1, 3-dioxane-4-acetate, a key intermediate for the preparation of CI-981, a highly potent, tissue selective inhibitor of HMG-CoA reductase
    • Brower, P.L.; Butler, D.E.; Deering, C.F.; Le Tung, V.; Millar, A.; Nanninga, T.N.; Roth, B.D. The synthesis of (4R-cis)-1, 1-dimethylethyl-6-cyanomethyl-2, 2-dimethyl-1, 3-dioxane-4-acetate, a key intermediate for the preparation of CI-981, a highly potent, tissue selective inhibitor of HMG-CoA reductase. Tetrahedron Lett. 1992, 33 (17), 2279-2282.
    • (1992) Tetrahedron Lett. , vol.33 , Issue.17 , pp. 2279-2282
    • Brower, P.L.1    Butler, D.E.2    Deering, C.F.3    Le Tung, V.4    Millar, A.5    Nanninga, T.N.6    Roth, B.D.7
  • 3
    • 0026504865 scopus 로고
    • The convergent synthesis of Ci-981, an optically active, highly potent, tissue selective inhibitor of HMG-CoA reductase
    • Baumann, K.L; Butler, D.E.; Deering, C.F.; Mennen, K.E.; Millar, A.; Nanninga, T.N.; Palmer, C.W.; Roth, B.D. The convergent synthesis of CI-981, an optically active, highly potent, tissue selective inhibitor of HMG-CoA reductase. Tetrahedron Lett. 1992, 33 (17), 2283-2284.
    • (1992) Tetrahedron Lett. , vol.33 , Issue.17 , pp. 2283-2284
    • Baumann, K.L.1    Butler, D.E.2    Deering, C.F.3    Mennen, K.E.4    Millar, A.5    Nanninga, T.N.6    Palmer, C.W.7    Roth, B.D.8
  • 4
    • 0037617205 scopus 로고    scopus 로고
    • Process for the Synthesis of (4R-cis)-1, 1-Dimethylethyl 6-cyanomethyl-2, 2-dimethyl-1, 3-dioxane-4-acetate. US Patent 5,103,024, April 07, 1992 (Warner-Lambert Co.)
    • Butler, D.E.; Millar, A. Process for the Synthesis of (4R-cis)-1, 1-Dimethylethyl 6-cyanomethyl-2, 2-dimethyl-1, 3-dioxane-4-acetate. US Patent 5,103,024, April 07, 1992 (Warner-Lambert Co.).
    • Butler, D.E.1    Millar, A.2
  • 5
    • 0038292757 scopus 로고    scopus 로고
    • Process for the Synthesis of (5R)-1, 1-Dimethylethyl 6-cyano-5-hydroxy-3-oxohexanoate. US Patent 5,155,251, October 13, 1992 (Warner-Lambert Co.)
    • Butler, D.E.; Le Tung, V.; Millar, A.; Nanninga, T.N. Process for the Synthesis of (5R)-1, 1-Dimethylethyl 6-cyano-5-hydroxy-3-oxohexanoate. US Patent 5,155,251, October 13, 1992 (Warner-Lambert Co.).
    • Butler, D.E.1    Le Tung, V.2    Millar, A.3    Nanninga, T.N.4
  • 6
    • 0037955235 scopus 로고    scopus 로고
    • Process for producing 6-cyanomethyl-2-dimethyl-1,3-dioxane-4-acetic acid derivatives. EP Appl. 1,077, 212 A1, April 28, 1999 (Kaneka Co.)
    • Mitsuda, M; Miyazaki, M.; Inoue, K. Process for producing 6-cyanomethyl-2-dimethyl-1,3-dioxane-4-acetic acid derivatives. EP Appl. 1,077, 212 A1, April 28, 1999 (Kaneka Co.).
    • Mitsuda, M.1    Miyazaki, M.2    Inoue, K.3
  • 8
    • 0029142910 scopus 로고
    • Practical large scale synthesis of tert-butyl (3R,5S)-6-hydroxy-3,5-O-isopropylidene-3,5-dihydroxy-hexanoate: Essential building block for HMG-CoA reductase inhibitors
    • Beck, G.; Jendralla, H.; Kesseler K. Practical large scale synthesis of tert-butyl (3R,5S)-6-hydroxy-3,5-O-isopropylidene-3,5-dihydroxy-hexanoate: essential building block for HMG-CoA reductase inhibitors. Synthesis 1995, 8, 1014-1018.
    • (1995) Synthesis , vol.8 , pp. 1014-1018
    • Beck, G.1    Jendralla, H.2    Kesseler, K.3
  • 9
    • 0037955242 scopus 로고    scopus 로고
    • Process for preparing optically active 2-[6-(hydroxymethyl)-1,3-dioxan-4-yl]acetic acid derivatives. WO 01/94,337, December 13, 2001 (Kaneka Co.)
    • Nishiyama, A.; Horikawa, M.; Yasohara, Y.; Ueyama, N.; Inoue, K. Process for preparing optically active 2-[6-(hydroxymethyl)-1,3-dioxan-4-yl]acetic acid derivatives. WO 01/94,337, December 13, 2001 (Kaneka Co).
    • Nishiyama, A.1    Horikawa, M.2    Yasohara, Y.3    Ueyama, N.4    Inoue, K.5
  • 10
    • 0021171455 scopus 로고
    • Synthesis of amphotericin B. 1. fragment A of the aglycon
    • Masamune, S.; Ma, P.; Okumoto, H; Ellingboe, J.W.; Ito, Y. Synthesis of amphotericin B. 1. fragment A of the aglycon. J. Org. Chem. 1984, 49 (15), 2834-2837.
    • (1984) J. Org. Chem. , vol.49 , Issue.15 , pp. 2834-2837
    • Masamune, S.1    Ma, P.2    Okumoto, H.3    Ellingboe, J.W.4    Ito, Y.5
  • 11
    • 0000498482 scopus 로고
    • A mild and simple enzymatic conversion of aldono- and aldurononitriles into the corresponding amides and/or carboxylic acids
    • de Raadt, A.; Griengl, H.; Klempier, N. A mild and simple enzymatic conversion of aldono- and aldurononitriles into the corresponding amides and/or carboxylic acids. J. Org. Chem. 1993, 58 (11), 3179-3184.
    • (1993) J. Org. Chem. , vol.58 , Issue.11 , pp. 3179-3184
    • De Raadt, A.1    Griengl, H.2    Klempier, N.3
  • 12
    • 0029044255 scopus 로고
    • Synthesis of artificial HMG-CoA reductase inhibitors based on the olefination strategy
    • Hiyama, T.; Minami, T.; Takahashi, K. Synthesis of artificial HMG-CoA reductase inhibitors based on the olefination strategy. Bull. Soc. Chem. Jpn. 1995, 68 (1), 364-372.
    • (1995) Bull. Soc. Chem. Jpn. , vol.68 , Issue.1 , pp. 364-372
    • Hiyama, T.1    Minami, T.2    Takahashi, K.3
  • 13
    • 84989478646 scopus 로고
    • Activated dimethyl sulfoxide: Useful reagents for synthesis
    • Mancuso, A.J.; Swern, D. Activated dimethyl sulfoxide: useful reagents for synthesis. Synthesis 1981, (3), 165-185.
    • (1981) Synthesis , Issue.3 , pp. 165-185
    • Mancuso, A.J.1    Swern, D.2
  • 14
    • 12644312578 scopus 로고
    • Oxidation of long-chain and related alcohols to carbonyls by dimethyl sulfoxide activated by oxalyl chloride
    • Mancuso, A.J.; Huang, S.-L.; Swern, D. Oxidation of long-chain and related alcohols to carbonyls by dimethyl sulfoxide activated by oxalyl chloride. J. Org. Chem. 1978, 43 (12), 2480-2482.
    • (1978) J. Org. Chem. , vol.43 , Issue.12 , pp. 2480-2482
    • Mancuso, A.J.1    Huang, S.-L.2    Swern, D.3
  • 15
    • 84989583620 scopus 로고
    • Pyridinium chlorochromate adsorbed on alumina as a selective oxidant for primary and secondary alcohols
    • Cheng, Y.S.; Liu, W.-L.; Chen, S.H. Pyridinium chlorochromate adsorbed on alumina as a selective oxidant for primary and secondary alcohols. Synthesis 1980, 3, 223-224.
    • (1980) Synthesis , vol.3 , pp. 223-224
    • Cheng, Y.S.1    Liu, W.-L.2    Chen, S.H.3
  • 16
    • 33845378126 scopus 로고
    • A nitrile oxide based entry to 2,3-dihydropyran-4-ones. Synthesis of a protected version of "compactin lactone" in racemic and optically active forms
    • Kozikowski, A.P.; Li, C.-S. A nitrile oxide based entry to 2,3-dihydropyran-4-ones. Synthesis of a protected version of "compactin lactone" in racemic and optically active forms. J. Org. Chem. 1985, 50 (6), 778-785.
    • (1985) J. Org. Chem. , vol.50 , Issue.6 , pp. 778-785
    • Kozikowski, A.P.1    Li, C.-S.2
  • 17
    • 37049104596 scopus 로고
    • An examination of the extent of diastereofacial selection in the reactions of a chiral nitrile oxide with achiral alkenes: A route to β-hydroxy carboxylic acids
    • Kozikowski, A.P.; Kitagawa, Y.; Springer, J.P. An examination of the extent of diastereofacial selection in the reactions of a chiral nitrile oxide with achiral alkenes: a route to β-hydroxy carboxylic acids. J. Chem. Soc., Chem. Commun. 1983, 23, 1460-1462.
    • (1983) J. Chem. Soc., Chem. Commun. , vol.23 , pp. 1460-1462
    • Kozikowski, A.P.1    Kitagawa, Y.2    Springer, J.P.3
  • 18
    • 49349140100 scopus 로고
    • Nitroalkane synthesis. A convenient method for aldehyde reductive nitromethylation
    • Wollenberg, R.H.; Miller, S.J. Nitroalkane synthesis. A convenient method for aldehyde reductive nitromethylation. Tetrahedron Lett. 1978, 19, 3219-3222.
    • (1978) Tetrahedron Lett. , vol.19 , pp. 3219-3222
    • Wollenberg, R.H.1    Miller, S.J.2
  • 19
    • 0000012139 scopus 로고
    • Nitroalkanes from conjugated nitroalkenes by reduction with complex hydrides
    • Schechter, H.; Ley, D.L.; Robertson, E.B. Nitroalkanes from conjugated nitroalkenes by reduction with complex hydrides. J. Am. Chem. Soc. 1956, 78, 4984-4991.
    • (1956) J. Am. Chem. Soc. , vol.78 , pp. 4984-4991
    • Schechter, H.1    Ley, D.L.2    Robertson, E.B.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.