Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2016, Issue 8, Pages 1520-1532Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201600071
Keywords
Protecting groups; Neighbouring group participation; Glycosylation; Diastereoselectivity
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Funding
- Engineering and Physical Sciences Research Council (EPSRC) (DTA award)
- Biomolecular Interaction Centre at the University of Canterbury
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A series of glycosyl donors possessing a (thiophen2-yl) methyl ether protecting group at position 2 were synthesised and the effect of the protecting group pattern of other hydroxyls on the stereochemical outcome of glycosylation was investigated. Studies revealed optimal a-selectivity for glycosylation using a fully armed tri-benzylated donor, whilst other protecting group patterns were significantly less effective. Lowtemperature NMR studies of both fully armed and fully disarmed donors revealed the intermediacy of cyclised sulfonium ion intermediates. Reaction conditions were developed which allowed removal of the (thiophen-2-yl) methyl ether protecting group either selectively, or together with benzyl ethers.
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