862537-80-2Relevant academic research and scientific papers
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.
Revisiting the armed-disarmed concept rationale: S-benzoxazolyl glycosides in chemoselective oligosaccharide synthesis
Kamat, Medha N.,Demchenko, Alexei V.
, p. 3215 - 3218 (2007/10/03)
(Chemical Equation Presented) It has been discovered that 2-O-benzyl-3,4,6-tri-O-acyl SBox glycosides are significantly less reactive than even "disarmed" peracylated derivatives. This finding has been applied to the synthesis of various oligosaccharides,
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
