501416-35-9Relevant academic research and scientific papers
Glycosyl thioimidates in a highly convergent one-pot strategy for oligosaccharide synthesis
Pornsuriyasak, Papapida,Demchenko, Alexei V.
, p. 433 - 439 (2005)
Application of two classes of thioimidoyl derivatives, S-benzoxazolyl (SBox) and S-thiazolyl (STaz) glycosides to selective activation over thioglycosides is described. These results allowed us to synthesize a tetrasaccharide derivative using a leaving group differentiated one-pot strategy in 73% yield over three sequential glycosylation steps.
On orthogonal and selective activation of glycosyl thioimidates and thioglycosides: Application to oligosaccharide assembly
Kaeothip, Sophon,Demchenko, Alexei V.
scheme or table, p. 7388 - 7398 (2011/11/11)
Discrimination among S-thiazolinyl (STaz), S-benzoxazolyl (SBox), and S-ethyl anomeric leaving groups was achieved by fine-tuning activation conditions. Preferential glycosidation of a certain leaving group is determined neither by the strength of the act
S-benzoxazolyl as a stable protecting moiety and a potent anomeric leaving group in oligosaccharide synthesis
Kamat, Medha N.,De Meo, Cristina,Demchenko, Alexei V.
, p. 6947 - 6955 (2008/02/11)
(Chemical Equation Presented) As a part of a program for developing new versatile building blocks for stereoselective glycosylation and convergent oligosaccharide synthesis, we demonstrated that S-benzoxazolyl (SBox) glycosides are stable toward major protecting group manipulations employed in carbohydrate chemistry. On the other hand, they can be glycosidated under relatively mild reaction conditions to afford either 1,2-trans or 1,2-cis-linked disaccharides. Selective and chemoselective activations of the SBox moiety were also proved to be feasible, which was demonstrated by synthesizing a number of oligosaccharide sequences.
S-benzoxazolyl (SBox) glycosides as novel, versatile glycosyl donors for stereoselective 1,2-cis glycosylation
Demchenko, Alexei V.,Malysheva, Nelli N.,De Meo, Cristina
, p. 455 - 458 (2007/10/03)
(Matrix presented) Novel glycosyl donors, S-benzoxazolyl (SBox) glycosides, have been synthesized, tested toward various protecting group manipulations, and applied to the highly stereoselective 1,2-cis glycosylation. These compounds fulfill the requireme
