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J Org Chem. 2014 May 16;79(10):4718-26. doi: 10.1021/jo500503r. Epub 2014 May 2.

Stereoselective synthesis of a sulfated tetrasaccharide corresponding to a rare sequence in the galactofucan isolated from Sargassum polycystum.

Author information

1
Shanghai Engineering Research Centre of Molecular Therapeutics and New Drug Development, and Department of Chemistry, East China Normal University , Shanghai, 200062, PR China.

Abstract

The first chemical synthesis of a highly sulfated tetrasaccharide 1, as the rare sequence in the galactofucan isolated from the brown alga Sargassum polycystum, was achieved in a convergent and stereoselective manner. The key features of the synthetic strategy include construction of multiple contiguous 1,2-cis glycosidic bonds and [2 + 2] assembly based on the rationally developed d-galactose building block 6. The synthesized oligosaccharides were fully characterized using a combination of coupled-HSQC and other 2D NMR techniques.

PMID:
24766314
DOI:
10.1021/jo500503r
[Indexed for MEDLINE]

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