Novel Regioselective Glycosylations for the Convergent and Chemoselective Assembly of Oligosaccharides

Synlett

Volumn 1997, Issue 7, 1997, Pages 809-811

  Boons, Geert Jan ^a   Zhu, Tong ^a  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542744880     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-5767     Document Type: Article

References (32)

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28. A few examples have been reported in which a glycosyl donor contained a hydroxyl. However, this feature of the glycosyl donor was not exploited in a convergent synthesis of an oligosaccharide. See for example: a) S. Danishefsky, J. Am. Chem. Soc., 117 (1995) 7840;
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32. Glycosyl donor 17 was also coupled with methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside and the corresponding trisaccharide was obtained in a high yield. A trisaccharide was also isolated in an excellent yield when 2 was coupled was with a partially benzoylated cellobiose derivative having 6′-hydroxyl. These experiments show that the difference in steric environment between the 6-hydroxyl of the glucoside and galactoside do not account for the observed chemoselectivity.