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Volumn 69, Issue 5, 2004, Pages 1625-1628

Variable Strategy toward Carbasugars and Relatives. 6. Diastereoselective Synthesis of 2-Deoxy-2-amino-5a-carba-β-L-mannopyranuronic Acid and 2-Deoxy-2-amino-5a-carba-β-L-mannopyranose

Author keywords

[No Author keywords available]

Indexed keywords

SUGARS; SYNTHESIS (CHEMICAL);

EID: 1442348962     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0357216     Document Type: Article
Times cited : (23)

References (38)
  • 2
    • 0034678033 scopus 로고    scopus 로고
    • For recent reviews on diversity-oriented synthesis, see: (a) Schreiber, S. L. Science 2000, 287, 1964-1969.
    • (2000) Science , vol.287 , pp. 1964-1969
    • Schreiber, S.L.1
  • 4
    • 77957047686 scopus 로고    scopus 로고
    • Atta-ur-Rahman, Ed.; Elsevier Science B.V.: Amsterdam, The Netherlands
    • For recent reviews on carbasugars and relatives, see: (a) Rassu, G.; Auzzas, L.; Pinna, L.; Battistini, L.; Curti, C. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science B.V.: Amsterdam, The Netherlands, 2003; Vol. 29, pp 449-520.
    • (2003) Studies in Natural Products Chemistry , vol.29 , pp. 449-520
    • Rassu, G.1    Auzzas, L.2    Pinna, L.3    Battistini, L.4    Curti, C.5
  • 24
    • 0034614462 scopus 로고    scopus 로고
    • (e) Lombardo, M.; Trombini, C. Tetrahedron 2000, 56, 323-326. See also: Dilman, A. D.; Ioffe, S. L. Chem. Rev. 2003, 103, 733-772.
    • (2000) Tetrahedron , vol.56 , pp. 323-326
    • Lombardo, M.1    Trombini, C.2
  • 25
    • 0037363116 scopus 로고    scopus 로고
    • (e) Lombardo, M.; Trombini, C. Tetrahedron 2000, 56, 323-326. See also: Dilman, A. D.; Ioffe, S. L. Chem. Rev. 2003, 103, 733-772.
    • (2003) Chem. Rev. , vol.103 , pp. 733-772
    • Dilman, A.D.1    Ioffe, S.L.2
  • 26
    • 1442267471 scopus 로고    scopus 로고
    • note
    • A screen of various silyl trifiates (TMSOTf, TESOTf, TBSOTf, TIPSOTf) indicated commercial TBSOTf to be the optimal promoter in this reaction.
  • 27
    • 1442292012 scopus 로고    scopus 로고
    • note
    • A plausible transition state to anti,anti-configured adduct 5 involves a synclinal-type approach of the silyloxy diene C(5) re-face to the C(1) si-face of the imine acceptor according to a relatively uncongested open-chain (Felkin-Ahn) model described here.
  • 28
    • 1442292010 scopus 로고    scopus 로고
    • note
    • In truth, the alternative cyclization protocol A to B was actually attempted. However, the extremely low yields obtained in elaborating adduct 6 into a suitably protected aldehyde lactone of type A (i.e., NPG = Cbz; OPG = TES) forced us to back down from this strategic option and follow the second and more fruitful route reported in this study.
  • 30
    • 0346780619 scopus 로고    scopus 로고
    • For a recent example of a silylative Mukaiyama intermolecular aldol reaction with TBSOTf and Hünig's base, see: Jung, M. E.; van den Heuvel, A. Org. Lett. 2003, 5, 4705-4707. See also: Evans, D. A.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2002, 124, 392-393.
    • (2003) Org. Lett. , vol.5 , pp. 4705-4707
    • Jung, M.E.1    Van Den Heuvel, A.2
  • 31
    • 0037160423 scopus 로고    scopus 로고
    • For a recent example of a silylative Mukaiyama intermolecular aldol reaction with TBSOTf and Hünig's base, see: Jung, M. E.; van den Heuvel, A. Org. Lett. 2003, 5, 4705-4707. See also: Evans, D. A.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2002, 124, 392-393.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 392-393
    • Evans, D.A.1    Tedrow, J.S.2    Shaw, J.T.3    Downey, C.W.4
  • 32
    • 1442316466 scopus 로고    scopus 로고
    • note
    • Stereochemical proofs for 12, as well as 1 and 2·HCl, are compiled in the Supporting Information (Tables S1-S3).
  • 37
    • 1442341005 scopus 로고    scopus 로고
    • note
    • Interestingly, 1 and ent-1 can be viewed as new, locked hydroxyethylene isosteres of D-Ser-D-Ser and L-Ser-L-Ser dipeptides, respectively.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.