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Synfacts 2018; 14(01): 0037
DOI: 10.1055/s-0036-1591077
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Gold(I)-Catalyzed Stereoselective Synthesis of Deoxyglycosides

Contributor(s):
Hisashi Yamamoto
,
Takahiro Sawano
Palo-Nieto C. Sau A. Galan MC. * University of Bristol, UK
Gold(I)-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals.

J. Am. Chem. Soc. 2017;
139: 14041-14044
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Further Information

Publication History

Publication Date:
15 December 2017 (online)

 
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Key words

gold catalysis - deoxyglycosides - glycals - alkoxylation

Significance

Deoxyhexose structures can be found in a wide range of natural products. The authors have developed an α-stereoselective catalytic synthesis of deoxyglycosides from glycals by using Au(I)/AgOTf.


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Comment

The reaction can be applied to a broad range of glycals and alcohols to give α-deoxyglycosides in high yields and with excellent selectivity. The utility of the reaction was demonstrated by the synthesis of oligosaccharides through the coupling reaction followed by deprotection.


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