90357-89-4Relevant articles and documents
Stereoselective O-Glycosylations by Pyrylium Salt Organocatalysis**
Holmstr?m, Thomas,Nielsen, Michael Martin,Pedersen, Christian Marcus
supporting information, (2021/12/30)
Despite many years of invention, the field of carbohydrate chemistry remains rather inaccessible to non-specialists, which limits the scientific impact and reach of the discoveries made in the field. Aiming to increase the availability of stereoselective
Self-Promoted Glycosylation for the Synthesis of β-N-Glycosyl Sulfonyl Amides
Ma?a, Patrycja,Pedersen, Christian Marcus
, p. 5685 - 5689 (2021/08/30)
N-Glycosyl N-sulfonyl amides have been synthesized by a self-promoted glycosylation, i. e. without any catalysts, promotors or additives. When the reactions were carried out at lower temperatures a mixture of N- and O-glycosides were observed, where the latter rearranged to give the β-N-glycosides at elevated temperatures. By this method sulfonylated asparagine derivatives can be selectively β-glycosylated in high yields by trichloroacetimidate glycosyl donors of different reactivity including protected glucosamine derivatives. The chemoselectivity in the glycosylations as well as the rearrangements from O-glycosides to β-N-glycosides gives information of the glycosylation mechanism. This method gives access to glycosyl sulfonyl amides under mild conditions.
Chemoselectivity in Self-Promoted Glycosylation: N- vs. O-Glycosylation
Pedersen, Christian Marcus,Pinna, Alessandro
supporting information, (2020/06/23)
Self-promoted glycosylation using trichloroacetimidates and sulfonamides have recently been developed. In this communication, we study the parameters controlling the chemoselectivity between a nucleophilic sulfonamide nitrogen and an alcohol, both contain
