S-thiazolinyl (STaz) glycosides as versatile building blocks for convergent selective, chemoselective, and orthogonal oligosaccharide synthesis.
In the aim of developing new procedures for efficient oligosaccharide assembly, a range of S-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. Moreover, 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.
Pornsuriyasak
Papapida
P
Department of Chemistry and Biochemistry, University of Missouri--St. Louis, One University Boulevard, St. Louis, Missouri 63121, USA.
Demchenko
Alexei V
AV
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D013379:Substrate Specificity; D013844:Thiazoles / Q000737:chemistry*
D006027:Glycosides; D009844:Oligosaccharides; D013844:Thiazoles