AI Article Synopsis
- A linear strategy was devised to synthesize the tetrasaccharide repeating unit of the O-polysaccharide from Azospirillum brasilense SR80.
- The synthesis involved stepwise glycosylation, where thioglycoside donors, activated by NIS and La(OTf)3, produced the target tetrasaccharide with high stereoselectivity.
- Phthalimido was utilized as a precursor to create the required acetamido group, ensuring the formation of a 1,2-trans glycosidic linkage.
Article Abstract
A linear strategy has been developed for the synthesis of the tetrasaccharide repeating unit of the O-polysaccharide from Azospirillum brasilense SR80. Stepwise glycosylation of the rationally protected thioglycoside donors activated by NIS in the presence of La(OTf)3 furnished the target tetrasaccharide. The glycosylation reactions resulted in the formation of the desired linkage with absolute stereoselectivity and afforded the required derivatives in good to excellent yields. The phthalimido group has been used as the precursor of the desired acetamido group to meet the requirement of 1,2-trans glycosidic linkage.
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| http://dx.doi.org/10.1016/j.carres.2015.01.008 | DOI Listing |
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