Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 18, Pages 7388-7398Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo201117s
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- NIGMS [GM077170]
- NIAID [AI067494]
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Discrimination among S-thiazolinyl (STaz), S-benzoxazolyl (SBox), and S-ethyl anomeric leaving groups was achieved by fine-tuning activation conditions. Preferential glycosidation of a certain leaving group is determined neither by the strength of the activating reagent nor by the stability of the leaving group itself; instead, the type of activation plays the key role. The activation conditions established herein were applied to a sequential five-step synthesis of a hexasaccharide using six monosaccharide building blocks equipped with six different leaving groups.
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