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Tetrahedron Letters
Volumn 34, Issue 52, 1993, Pages 8523-8526
Dispiroketals in synthesis (Part 5): A new opportunity for oligosaccharide synthesis using differentially activated glycosyl donors and acceptors
Author keywords

[No Author keywords available]
Indexed keywords

OLIGOSACCHARIDE;
EID: 0027772575     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)61375-8     Document Type: Article
Times cited : (85)
References (22)
  • 1
    • 84918722487 scopus 로고    scopus 로고
    • For part 4 see Boons G.J., Entwistle D.A., Ley S.V., Tetrahedron Lett., in press.
  • 12
    • 84918734953 scopus 로고    scopus 로고
    • Owing to the ease of preparation of ethyl l-thio-β-galactoside and ethyl l-thio-α-mannoside they were selected as starting materials. We are also investigating the effect of the anomeric configuration of the thioglycoside on the anomeric leaving group ability.
  • 14
    • 84918737759 scopus 로고    scopus 로고
    • All new compounds gave satisfactory spectroscopic and analytical data.
  • 15
    • 84918757097 scopus 로고    scopus 로고
    • Ley S.V., Boons G.J., Leslie R., Woods M., Hollinshead D.M., Synthesis, in press.
  • 16
    • 84918751076 scopus 로고    scopus 로고
    • Preparation of compound 9: Regioselective silylation of l-thio-α-D-mannopyranoside with tert-butyldiphenylsilyl chloride (TBDPSCl), triethylamine and catalytic dimethylaminopyridine in DMF followed by protection of the cis diol as an isopropylidene functionality and benzylation with benzyl bromide and sodium hydride in DMF gave fully protected l-thio- 4-O-benzyl-2,3-di-O-isopropylidene-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside. Cleavage of the isopropylidene group of the fully protected compound with acetic acid/water followed by regioselective benzoylation under phase transfer conditions gave target compound 9.
  • 19
    • 84918727354 scopus 로고    scopus 로고
    • 14 by silylation with TBDMSCl in pyridine followed by regioselective desilylation of the TBDMS group at the anomeric centre with TBAF in THF/acetic acid and conversion of the resulting anomeric alcohol into the trichloroacetimidate by treatment with trichloroacetonitrile and potassium carbonate.
  • 21
    • 85064401100 scopus 로고
    • Microbial Oxidation in Synthesis: Preparation of a Potential Insulin Mimic from Benzene
    • (1992) Synlett , pp. 997
    • Ley1    Yeung2
  • 22
    • 84918759373 scopus 로고    scopus 로고
    • 3), 3.76 - 3.41, 16 H, m, H-1, H-3, H-6a,b′, H-3‴, H-4‴, H-5‴, H-2, [[Truncated]]

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.