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Volumn , Issue 4, 2004, Pages 609-614

An effective sialylation method using N-Troc- and N-Fmoc-protected β-thiophenyl sialosides and application to the one-pot two-step synthesis of 2,6-sialyl-T antigen

Author keywords

Glycopeptides; Glycosyl amino acids; One pot glycosylation; Sialic acids; Thioglycosides

Indexed keywords

2,6 SIALYL T ANTIGEN; ALCOHOL; AMINO ACID; ANTIGEN; BETA THIOPHENYLSIALOSIDE; GLYCOPEPTIDE; SIALIC ACID DERIVATIVE; THIOGLYCOSIDE; UNCLASSIFIED DRUG;

EID: 1642338668     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-817759     Document Type: Article
Times cited : (52)

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    • For the related approaches using GalNAcα(1→3)-Ser or -Thr derivatives as building blocks, see: (a) Nakahara, Y.; Iijima, H.; Ogawa, T. Tetrahedron Lett. 1994, 35, 3321. (b) Liebe, B.; Kunz, H. Tetrahedron Lett. 1994, 35, 8777. (c) Meinjohanns, E.; Meldal, M.; Paulsen, H.; Schleyer, A.; Bock, K. J. Chem. Soc., Perkin Trans. 1 1996, 985. (d) Liebe, B.; Kunz, H. Angew. Chem. Int. Ed. 1997, 36, 2830. (e) Chen, X.-T.; Sames, D.; Danishefsky, S. J. J. Am. Chem. Soc. 1998, 120, 7760.
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    • note
    • 1H NMR measurement of the isolated isomers according to empirical rule.
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    • note
    • The α/β ratio was determined by HPLC analysis based on refractive index detection (Eluent: hexane/2-propanol = 95:5, 3.0 mL/min; Retention time: α-isomer 12.9 min, β-isomer 16.1 min).


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