Zhang, Yunqin; He, Haiqing; Chen, Zixi; Huang, Yingying; Xiang, Guisheng; Li, Penghua; Yang, Xingkuan; Lu, Gang; Xiao, Guozhi published the artcile< Merging Reagent Modulation and Remote Anchimeric Assistance for Glycosylation: Highly Stereoselective Synthesis of α-Glycans up to a 30-mer>, SDS of cas: 4064-06-6, the main research area is branched oligosaccharide preparation glycosylation reagent modulation anchimeric assistance; 1,2-cis glycosylation; reagent modulation; remote anchimeric assistance; structure elucidation; synthetic methods.
The efficient synthesis of long, branched, and complex carbohydrates containing multiple 1,2-cis glycosidic linkages is a long-standing challenge. Here, we report a merging reagent modulation and 6-O-levulinoyl remote anchimeric assistance glycosylation strategy, which is successfully applied to the first highly stereoselective synthesis of the branched Dendrobium Huoshanense glycans and the linear Longan glycans containing up to 30 contiguous 1,2-cis glucosidic bonds. DFT calculations shed light on the origin of the much higher stereoselectivities of 1,2-cis glucosylation with 6-O-levulinoyl group than 6-O-acetyl or 6-O-benzoyl groups. Orthogonal one-pot glycosylation strategy based on glycosyl ortho-alkynylbenzoates and ortho-(1-phenylvinyl)benzoates has been demonstrated in the efficient synthesis of complex glycans, precluding such issues as aglycon transfer inherent to orthogonal one-pot synthesis based on thioglycosides.
Angewandte Chemie, International Edition published new progress about Dendrobium catenatum. 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, SDS of cas: 4064-06-6.
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