A new glycosylation method using glycosyl donors substituted by enol ether as a leaving group

Tetrahedron Letters

Volumn 40, Issue 8, 1999, Pages 1531-1534

  Osa, Yumiko ^a   Takeda, Kazuyoshi ^a,b   Sato, Tomoko ^a   Kaji, Eisuke ^a   Mizuno, Yoshihisa ^a   Takayanagi, Hiroaki ^a  

^a KITASATO UNIVERSITY   (Japan)

^b EBARA CORPORATION   (Japan)

Author keywords

Enol ether; Glycosyl donors; Glycosylation; Trimethylsilyl triflate

Indexed keywords

ALKYNE; CARBONYL DERIVATIVE; ETHER DERIVATIVE; HYDROXYL GROUP; KETONE; OLIGOSACCHARIDE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; GLYCOSYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0033582681     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02703-8     Document Type: Article

References (12)

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6. 3), 99 (C-1).
7. 3), 167.5 (C=O).
8. CH=CH = 12.5 Hz.
9. 3 was observed in 2.98%, and 10% NOE was observed for the anomeric proton and =CH. No NOE was observed between the methyl group and the anomeric proton or =CH. These NOEs showed that the donor (5 α, 5β) was in E-form. The other donors gave similar results. (Equation presented)
10. 4), and then, evaporated. The residue was purified by silica-gel column chromatography (hexane:AcOEt=5:2) to give an α,β-mixture of the product as a syrup (Yield 44.2 mg, 82%).
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