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Volumn 51, Issue 8, 2010, Pages 1209-1212

Hydroxyl group orientation affects hydrolysis rates of methyl α-septanosides

Author keywords

[No Author keywords available]

Indexed keywords

GALACTOSE; GLUCOSE; HEPTOSE; HYDROXYL GROUP; MANNOSE; METHYL ALPHA SEPTANOSIDE DERIVATIVE; OXEPINE DERIVATIVE; PYRANOSIDE; UNCLASSIFIED DRUG;

EID: 74049098362     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.12.109     Document Type: Article
Times cited : (12)

References (32)
  • 8
    • 74049087184 scopus 로고    scopus 로고
    • note
    • The oxacarbenium in these reactions likely arises from the 1,2-anhydroseptanose intermediate. A methyl β-septanoside that was subjected to the reaction conditions did not anomerize to the methyl α-septanoside. See the Supplementary data for details.
  • 12
    • 74049114682 scopus 로고    scopus 로고
    • note
    • The Supplementary data contains MS values for the hydrolysis products.
  • 15
    • 0007003020 scopus 로고
    • 1H NMR spectra from which kinetics data were obtained. See also:
    • 1H NMR spectra from which kinetics data were obtained. See also:. Haworth W.N., Owen L.N., and Smith F. J. Chem. Soc. (1941) 88
    • (1941) J. Chem. Soc. , pp. 88
    • Haworth, W.N.1    Owen, L.N.2    Smith, F.3
  • 18
    • 33749480880 scopus 로고    scopus 로고
    • Mechanisms for Nucleophilic Aliphatic Substitution at Glycosides
    • Richard J.P. (Ed), Academic Press, London, UK
    • Horenstein N.A. Mechanisms for Nucleophilic Aliphatic Substitution at Glycosides. In: Richard J.P. (Ed). Advances in Physical Organic Chemistry Vol. 41 (2006), Academic Press, London, UK 275-314
    • (2006) Advances in Physical Organic Chemistry , vol.41 , pp. 275-314
    • Horenstein, N.A.1
  • 19
    • 74049156476 scopus 로고    scopus 로고
    • note
    • The Supplementary data contains kinetics traces.
  • 20
    • 74049149993 scopus 로고    scopus 로고
    • note
    • Methyl α-septanoside 14 shares common stereochemistry at C2(3), C(4), C5(6) (septanose numbering) with 23 and they are therefore considered counterparts here. Similarly, 15 is linked to 24 and 16 to 25.
  • 21
    • 0002174114 scopus 로고    scopus 로고
    • Monosaccharides: Geometry and Dynamics
    • Finch P. (Ed), Kluwer, Dordrecht, The Netherlands
    • French A.D., and Finch P. Monosaccharides: Geometry and Dynamics. In: Finch P. (Ed). Carbohydrates: Structures, Syntheses, and Dynamics (1999), Kluwer, Dordrecht, The Netherlands 1-46
    • (1999) Carbohydrates: Structures, Syntheses, and Dynamics , pp. 1-46
    • French, A.D.1    Finch, P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.