365455-43-2Relevant academic research and scientific papers
Efficient methods for glycosidations with glycals - A key intermediate for the synthesis of mucin core 1-type O-glycan
Geiger, Jürgen,Barroca, Nadine,Schmidt
, p. 836 - 840 (2007/10/03)
The use of glycals as acceptors in glycosylation reactions is hampered by their sensitivity to acids. We report here on the successful use of mild Lewis acid [Sn(OTf)2] as catalyst for the glycosylation with O-glycosyl trichloroacetimidates and on the development of this method to construct a key intermediate for the synthesis of mucin type O-glycans. To this end, chemoselective nitration of O-glycosylated glycals, stereoselective threonine addition, and reduction of the nitro group to the amino group by an efficient procedure avoiding the use of an expensive catalyst was performed.
Nitroglycal concatenation: A broadly applicable and efficient approach to the synthesis of complex O-glycans
Winterfeld, Gottfried A.,Schmidt, Richard R.
, p. 2654 - 2657 (2007/10/03)
Base-catalyzed glycosylations provide the basis for a new and general entry to the synthesis of mucin-type O-glycans. The desired α-linked 2-acetamidoglycosyl amino acids B are accessible selectively starting from glycals of type A. Fmoc = 9-fluorenylmeth
