4.8 Article

Unexpected Orthogonality of S-Benzoxazolyl and S-Thiazolinyl Glycosides: Application to Expeditious Oligosaccharide Assembly

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卷 11, 期 4, 页码 799-802

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AMER CHEMICAL SOC
DOI: 10.1021/ol802740b

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  1. NIGMS NIH HHS [R15 GM077170, GM077170, R15 GM077170-01] Funding Source: Medline

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Thorough mechanistic studies of the alkylation pathway for the activation of glycosyl thioimidates have led to the development of the thioimidate-only orthogonal strategy. Discrimination among S-thiazolinyl (STaz) and S-benzoxazolyl (SBox) anomeric leaving groups was achieved by fine-tuning of the activation conditions. Preferential glycosidation of a certain thioimidate is not simply determined by the strength of activating reagents; instead, the type of activation-direct vs indirect-comes to the fore and plays the key role.

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