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Volumn 70, Issue 10, 2005, Pages 3988-3996

α-N-acetylmannosamine (ManNAc) synthesis via rhodium(II)-catalyzed oxidative cyclization of glucal 3-carbamates

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CATALYSIS; CATALYSTS; DERIVATIVES; IODINE COMPOUNDS; OXIDATION; RHODIUM; SYNTHESIS (CHEMICAL);

EID: 18744398143     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0500129     Document Type: Conference Paper
Times cited : (44)

References (86)
  • 32
    • 0042912996 scopus 로고    scopus 로고
    • Review of iminoiodinanes in C-N bond formation; Dauban, P.; Dodd, R. H. Synlett 2003, 1571-1586.
    • (2003) Synlett , pp. 1571-1586
    • Dauban, P.1    Dodd, R.H.2
  • 36
    • 18744397362 scopus 로고    scopus 로고
    • Crystallographic data (excluding structure factors) for 8α have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC-254675. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.; fax +44 1223 336033; e-mail deposit@ccdc.cam.ac.uk).
  • 37
    • 0026848778 scopus 로고
    • H1,H2 couplings (0 Hz for the α-anomers, 3 Hz for the β-anomers) are observed in the conformationally analogous 2,3-O-carbonates of manno- and rhamnopyranosides: (a) Günther, W.; Kunz, H. Carbohydr. Res. 1992, 228, 217-241.
    • (1992) Carbohydr. Res. , vol.228 , pp. 217-241
    • Günther, W.1    Kunz, H.2
  • 42
    • 2842528404 scopus 로고    scopus 로고
    • We are investigating mechanistic possibilities for dihydro-4-pyranone production, including initial iodonium formation at the glycal C=C and elimination of a proton from C3 or C3 hydride transfer to the carbonyl oxygen of a metallanitrene intermediate. Compare: (a) Kirschning, A. Eur. J. Org. Chem. 1998, 2267-2274.
    • (1998) Eur. J. Org. Chem. , pp. 2267-2274
    • Kirschning, A.1
  • 46
    • 18744390150 scopus 로고    scopus 로고
    • note
    • 3) or after N-acylation of 2α.
  • 50
    • 18744392656 scopus 로고    scopus 로고
    • note
    • Characterization data and isolated yields for the iodoetherification byproducts 30-34 are included in the Supporting Information.
  • 51
    • 1542714412 scopus 로고
    • Thatcher, G. R. J., Ed.; ACS Symposium Series 539; American Chemical Society: Washington, DC, and references therein
    • (a) Andrews, C. W.; Fraser-Reid, B.; Bowen, J. P. In The Anomeric Effect and Associated Stereoelectronic Effects; Thatcher, G. R. J., Ed.; ACS Symposium Series 539; American Chemical Society: Washington, DC, 1993; pp 114-125, and references therein.
    • (1993) The Anomeric Effect and Associated Stereoelectronic Effects , pp. 114-125
    • Andrews, C.W.1    Fraser-Reid, B.2    Bowen, J.P.3
  • 72
    • 18744386505 scopus 로고    scopus 로고
    • note
    • 3SiOTf). (diagram presented).
  • 74
    • 18744369161 scopus 로고    scopus 로고
    • note
    • The latter pathway was demonstrated by isolation of the intermediate carbonate 24α and resubjection to the reaction conditions, warming above -15 °C, to give 25α along with cyclized 2α.
  • 75
    • 18744386810 scopus 로고    scopus 로고
    • note
    • 3 suggested that the altered ratio was due to differing carbonyl site selectivities between the anomers rather than more facile recyclization of the initially formed 25β alkoxide.
  • 86
    • 4544236616 scopus 로고    scopus 로고
    • For a promising example of de novo 2-mannosamine synthesis: Northrup, A. B.; MacMillan, D. W. C. Science 2004, 305, 1752-1755.
    • (2004) Science , vol.305 , pp. 1752-1755
    • Northrup, A.B.1    MacMillan, D.W.C.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.