636997-65-4

Upstream product

• 139574-31-5 C₆H₁₂O₅SC₂H₄(C₇H₄O)3 
• 744245-92-9 2-thiazolinyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside 
• 14218-11-2 2,3,4,6-tetra-O-benzoylglucosyl bromide 
• 91958-78-0 2-(β-D-glucopyranosylmercapto)-1,3-benzoxazole 
• 6044-27-5 benzoxazol-2-yl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 635727-37-6 2-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosylmercapto)-1,3-benzoxazole 

Downstream Products

• 635727-45-6 pent-4-enyl O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-benzoyl-β-D-galactopyranosyl)-(1->6)-3-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 

Relevant academic research and scientific papers

On orthogonal and selective activation of glycosyl thioimidates and thioglycosides: Application to oligosaccharide assembly

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

(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-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 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.

Glycosyl thioimidates in a highly convergent one-pot strategy for oligosaccharide synthesis

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.

S-benzoxazolyl (SBox) glycosides in oligosaccharide synthesis: Novel glycosylation approach to the synthesis of β-D-glucosides, β-D-galactosides, and α-D-mannosides

Per-acetylated and per-benzoylated S-benzoxazolyl (SBox) glycosides have been synthesized and applied to highly efficient 1,2-trans glycosylation. Complete stereoselectivities and remarkably high yields were achieved for the synthesis of β-D-glucosides, β