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Issue 23, 2018
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Diversified synthesis and α-selective glycosylation of 3-amino-2,3,6-trideoxy sugars

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Abstract

Attachment of various 3-aminodeoxy sugars to natural products or drugs is a prominent method for new drug development. However, access to structurally diversified 3-aminodeoxy sugars and glycosylation with aglycons are challenging. We synthesized a variety of unnatural 3-aminodeoxy sugars via diversified functionalization of a common glycal intermediate bearing a cyclic sulfamidate ketimine moiety. Based on these results, the α-selective glycosylation reactions of these 3-aminodeoxy sugars and the structural modification of diosgenin were further investigated.

Graphical abstract: Diversified synthesis and α-selective glycosylation of 3-amino-2,3,6-trideoxy sugars

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Publication details

The article was received on 01 Sep 2018, accepted on 11 Oct 2018 and first published on 11 Oct 2018


Article type: Research Article
DOI: 10.1039/C8QO00948A
Citation: Org. Chem. Front., 2018,5, 3391-3395
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    Diversified synthesis and α-selective glycosylation of 3-amino-2,3,6-trideoxy sugars

    J. Zeng, R. Wang, W. Yao, S. Zhang, G. Sun, Z. Liao, L. Meng and Q. Wan, Org. Chem. Front., 2018, 5, 3391
    DOI: 10.1039/C8QO00948A

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