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Volumn 13, Issue 16, 2002, Pages 1825-1832

Synthesis and desilylation of (2R,3S)-α-methyl-α-silyl-α,β-2,3-dihydroxycarboxylic methyl esters

Author keywords

[No Author keywords available]

Indexed keywords

2 TERT BUTYL 2,5 DIMETHYL 1,3 DIOXOLAN 4 ONE; 2 TERT BUTYL 5 METHYL 1,3 DIOXOLAN 4 ONE; ACETAL; ALCOHOL DERIVATIVE; ALKANOATE; ALKANOIC ACID; CHEMICAL COMPOUND; ESTER DERIVATIVE; LITHIUM ENOLATE; METHOXIDE SODIUM; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0037183412     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00440-8     Document Type: Article
Times cited : (11)

References (42)
  • 1
    • 0015701712 scopus 로고
    • Representative reviews and articles are: (a) Keller-Schierlein, W. Forstrch. Chem. Org. Naturtst. 1973, 30, 313; (b) Masamune, S.; Bates, G. S.; Corcoran, J. W. Angew. Chem., Int. Ed. Engl. 1977, 16, 585; (c) Heathcock, C. H.; Pirrung, M. C.; Young, S. D.; Hagen, J. P.; Jarvi, E. T.; Badertscher, U.; Märki. H. P.; Montgomery, S. H. J. Am. Chem. Soc. 1984, 106, 8161; (d) Stürmer, R. Liebigs Ann. Chem. 1991, 311.
    • (1973) Forstrch. Chem. Org. Naturtst. , vol.30 , pp. 313
    • Keller-Schierlein, W.1
  • 2
    • 0017530117 scopus 로고
    • Representative reviews and articles are: (a) Keller-Schierlein, W. Forstrch. Chem. Org. Naturtst. 1973, 30, 313; (b) Masamune, S.; Bates, G. S.; Corcoran, J. W. Angew. Chem., Int. Ed. Engl. 1977, 16, 585; (c) Heathcock, C. H.; Pirrung, M. C.; Young, S. D.; Hagen, J. P.; Jarvi, E. T.; Badertscher, U.; Märki. H. P.; Montgomery, S. H. J. Am. Chem. Soc. 1984, 106, 8161; (d) Stürmer, R. Liebigs Ann. Chem. 1991, 311.Heathcock, C. H.; Pirrung, M. C.; Young, S. D.; Hagen, J. P.; Jarvi, E. T.; Badertscher, U.; Märki. H. P.; Montgomery, S. H. J. Am. Chem. Soc. 1984, 106, 8161; (d) Stürmer, R. Liebigs Ann. Chem. 1991, 311.
    • (1977) Angew. Chem., Int. Ed. Engl. , vol.16 , pp. 585
    • Masamune, S.1    Bates, G.S.2    Corcoran, J.W.3
  • 3
    • 0001290346 scopus 로고
    • Representative reviews and articles are: (a) Keller-Schierlein, W. Forstrch. Chem. Org. Naturtst. 1973, 30, 313; (b) Masamune, S.; Bates, G. S.; Corcoran, J. W. Angew. Chem., Int. Ed. Engl. 1977, 16, 585; (c) Heathcock, C. H.; Pirrung, M. C.; Young, S. D.; Hagen, J. P.; Jarvi, E. T.; Badertscher, U.; Märki. H. P.; Montgomery, S. H. J. Am. Chem. Soc. 1984, 106, 8161; (d) Stürmer, R. Liebigs Ann. Chem. 1991, 311.Heathcock, C. H.; Pirrung, M. C.; Young, S. D.; Hagen, J. P.; Jarvi, E. T.; Badertscher, U.; Märki. H. P.; Montgomery, S. H. J. Am. Chem. Soc. 1984, 106, 8161; (d) Stürmer, R. Liebigs Ann. Chem. 1991, 311.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 8161
    • Heathcock, C.H.1    Pirrung, M.C.2    Young, S.D.3    Hagen, J.P.4    Jarvi, E.T.5    Badertscher, U.6    Märki, H.P.7    Montgomery, S.H.8
  • 4
    • 84986676607 scopus 로고
    • Representative reviews and articles are: (a) Keller-Schierlein, W. Forstrch. Chem. Org. Naturtst. 1973, 30, 313; (b) Masamune, S.; Bates, G. S.; Corcoran, J. W. Angew. Chem., Int. Ed. Engl. 1977, 16, 585; (c) Heathcock, C. H.; Pirrung, M. C.; Young, S. D.; Hagen, J. P.; Jarvi, E. T.; Badertscher, U.; Märki. H. P.; Montgomery, S. H. J. Am. Chem. Soc. 1984, 106, 8161; (d) Stürmer, R. Liebigs Ann. Chem. 1991, 311.Heathcock, C. H.; Pirrung, M. C.; Young, S. D.; Hagen, J. P.; Jarvi, E. T.; Badertscher, U.; Märki. H. P.; Montgomery, S. H. J. Am. Chem. Soc. 1984, 106, 8161; (d) Stürmer, R. Liebigs Ann. Chem. 1991, 311.
    • (1991) Liebigs Ann. Chem. , pp. 311
    • Stürmer, R.1
  • 23
    • 0033603378 scopus 로고    scopus 로고
    • In contrast to the enolate of 2, the enolate of 1 affords a self-addition product and several derived from thermal decomposition, see: (a) Battaglia, A.; Barbaro, G.; Guerrini, A.; Bertucci, C. J. Org. Chem. 1999, 64, 4643; (b) Battaglia, A.; Barbaro, G.; Guerrini, A.; Bertucci, C. Tetrahedron: Asymmetry 1997, 8, 2527; (c) Ref. 3b.
    • (1999) J. Org. Chem. , vol.64 , pp. 4643
    • Battaglia, A.1    Barbaro, G.2    Guerrini, A.3    Bertucci, C.4
  • 24
    • 0030790661 scopus 로고    scopus 로고
    • In contrast to the enolate of 2, the enolate of 1 affords a self-addition product and several derived from thermal decomposition, see: (a) Battaglia, A.; Barbaro, G.; Guerrini, A.; Bertucci, C. J. Org. Chem. 1999, 64, 4643; (b) Battaglia, A.; Barbaro, G.; Guerrini, A.; Bertucci, C. Tetrahedron: Asymmetry 1997, 8, 2527; (c) Ref. 3b.
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 2527
    • Battaglia, A.1    Barbaro, G.2    Guerrini, A.3    Bertucci, C.4
  • 25
    • 0005169358 scopus 로고    scopus 로고
    • note
    • In contrast to the enolate of 2, the enolate of 1 affords a self-addition product and several derived from thermal decomposition, see: (a) Battaglia, A.; Barbaro, G.; Guerrini, A.; Bertucci, C. J. Org. Chem. 1999, 64, 4643; (b) Battaglia, A.; Barbaro, G.; Guerrini, A.; Bertucci, C. Tetrahedron: Asymmetry 1997, 8, 2527; (c) Ref. 3b.
  • 26
    • 0005174045 scopus 로고    scopus 로고
    • 3 (8.0 mg) to of 7-10 (20 mg) shifted the C2-Me signal of the (2S,5R,1′R)-isomer at lower field (0.02 ppm) with respect to that of the (2R,5S,1′S)-enantiomer
    • 3 (8.0 mg) to of 7-10 (20 mg) shifted the C2-Me signal of the (2S,5R,1′R)-isomer at lower field (0.02 ppm) with respect to that of the (2R,5S,1′S)-enantiomer.
  • 30
    • 84984208956 scopus 로고
    • See: (a) Ladner, W. Chem. Ber. 1983, 116, 3413; (b) Bergel'son, L. D.; Dyatlovitskaya, E. V.; Tichy, M.; Voronkova, V. V. Izv. Akad. Nauk SSSR, Otd. Khim. Nauk 1962, 1612 [Chem Abstr. 1963, 58, 4416e].
    • (1983) Chem. Ber. , vol.116 , pp. 3413
    • Ladner, W.1
  • 32
    • 0005135131 scopus 로고    scopus 로고
    • For the synthesis of this mixture of dioxolanone alcohols, see Ref. 5
    • For the synthesis of this mixture of dioxolanone alcohols, see Ref. 5 .


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.