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Volumn 2, Issue 24, 2000, Pages 3797-3800

Highly Efficient and Practical Synthesis of 3,6-branched Oligosaccharides

Author keywords

[No Author keywords available]

Indexed keywords

OLIGOSACCHARIDE;

EID: 0034736309     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol000243w     Document Type: Article
Times cited : (52)

References (45)
  • 2
    • 0001094662 scopus 로고    scopus 로고
    • (a) Dwek, R. A. Chem. Rev. 1996, 96, 683-720.
    • (1996) Chem. Rev. , vol.96 , pp. 683-720
    • Dwek, R.A.1
  • 31
    • 85037505838 scopus 로고    scopus 로고
    • note
    • 2O (3 equiv) instead of BzCl in the aforementioned acylation step furnished the corresponding acetylated derivatives smoothly.
  • 32
    • 85037505971 scopus 로고    scopus 로고
    • note
    • We cannot give an unbeatable explanation for this regioselectivity. We found that the orientation of anomeric oxygen or sulfur atom is critical to the reaction outcomes. Generally, α-D-manno-, β-D-gluco- and β-D-galactopyranosides gave 3,6-disubstitutes products. Interestingly, α-D-glucopyranosides generate 2,6-disubstitutes while α-D-galactopyranosides gave 2,6- and 3,6-disubstituted mixtures.
  • 33
    • 85037495957 scopus 로고    scopus 로고
    • note
    • 3CO).
  • 36
    • 85037501116 scopus 로고    scopus 로고
    • note
    • We tried coupling reaction of 17 with 20 on small scale (around 100 mg of reactants) and disaccharide acceptor 21 was obtained in 4 h without adding extra TMSOTf. The same reaction condition was not suitable for larger reaction scale, thus more TMSOTf or trifluoroacetic acid was added into the reaction flask when TLC showed the first coupling reaction finished.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.