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Volumn 48, Issue 47, 2009, Pages 8896-8899

Phenylthiomethyl glycosides: Convenient synthons for the formation of azidomethyl and glycosylmethyl glycosides and their derivatives

Author keywords

Acetais; Glycosylation; Ligation; Staudinger reaction; Triazoles

Indexed keywords

ACETAIS; LIGATION; STAUDINGER REACTION; STAUDINGER REACTIONS; SYNTHONS; TRIAZOLES;

EID: 70449135143     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200904168     Document Type: Article
Times cited : (34)

References (54)
  • 2
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    • Angew. Chem. Int. Ed. 2001, 40, 2004-2021;
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 2004-2021
  • 5
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    • 0037119654 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2002, 41, 3449-3451.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 3449-3451
  • 25
    • 70449106546 scopus 로고    scopus 로고
    • note
    • We note that the use of more than 1.1. equivalent of silver triflate resulted in lower yields of product 3 and over activation leading, for example, to the formation of phenylthiomethoxymethyl glycosides. The moderate yields for the formation of 3 and 6 are to some extent the result of the relative instability of phenylthiomethanol under the coupling conditions.
  • 28
    • 70449129232 scopus 로고    scopus 로고
    • The moderate yield is most likely due to the persistence of thiophilic species in the reaction mixture after the preactivation step.
    • The moderate yield is most likely due to the persistence of thiophilic species in the reaction mixture after the preactivation step.
  • 30
    • 84987145542 scopus 로고
    • "reducing sugar" in methyl 3,6-di-O-(α-D-mannopyranosyl)- α-D-mannopyranoside, which are known to contribute substantially to binding
    • 3. The significantly reduced binding affinity exhibited by the two triazoles is attributed in part to the absence of the hydroxyl groups at C2 and C4 of the "reducing sugar" in methyl 3,6-di-O-(α-D- mannopyranosyl)-α-D-mannopyranoside, which are known to contribute substantially to binding. G. H. Veeneman, G. A. van der Marel, H. Vandenelst, J. H. van Boom, Recl. Trav. Chim. Pays-Bas 1990, 109, 449-451.
    • (1990) Recl. Trav. Chim. Pays-Bas , vol.109 , pp. 449-451
    • Veeneman, G.H.1    Van Der Marel, G.A.2    Vandenelst, H.3    Van Boom, J.H.4
  • 40
    • 67650474557 scopus 로고    scopus 로고
    • d) M. D. Best, Biochemistry 2009, 48, 6571-6584;
    • (2009) Biochemistry , vol.48 , pp. 6571-6584
    • Best, M.D.1
  • 48
    • 0002113451 scopus 로고
    • The basic structural unit of the "acetal glycosides" occurs naturally in the 1,1′-disaccharides, in sucrose, in the iridoid glycosides, and in the seco-iridoid glycosides, albeit in a some-what more complex form; a) L. F. Tietze, U. Niemeyer, P. Marx, K. H. Glusenkamp, L. Schwenen, Tetrahedron 1980, 36, 735-739;
    • (1980) Tetrahedron , vol.36 , pp. 735-739
    • Tietze, L.F.1    Niemeyer, U.2    Marx, P.3    Glusenkamp, K.H.4    Schwenen, L.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.