174777-55-0Relevant academic research and scientific papers
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-thiazolinyl (STaz) glycosides as versatile building blocks for convergent selective, chemoselective, and orthogonal oligosaccharide synthesis
Pornsuriyasak, Papapida,Demchenko, Alexei V.
, p. 6630 - 6646 (2008/09/17)
In the aim of developing new procedures for efficient oligosaccharide assembly, a range of 5-thiazolinyl (STaz) glycosides have been synthesized. These novel derivatives were evaluated against a variety of reaction conditions and were shown to be capable of being chemoselectively activated in the armed-disarmed fashion. More over, the S-thiazolinyl moiety exhibited a remarkable propensity for selective activation over other common leaving groups. Conversely, a variety of leaving groups could be selectively activated over the STaz moiety, which, in turn, allowed STaz/S-ethyl and STaz/S-phenyl orthogonal approaches. To demonstrate versatility of novel STaz derivatives, a number of oligosaccharide targets have been synthesized in a convergent selective, orthogonal, and chemoselective fashion.
