675876-42-3

Upstream product

• 1226524-10-2 phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactoside 
• 197663-12-0 phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thiol-D-galactopyranoside 
• 197663-19-7 phenyl-2-azido-2-deoxy-1-thio-D-galactopyranoside 
• 148416-94-8 phenyl-3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thio-β-D-galactopyranoside 
• 819798-39-5 phenyl-2-azido-2-deoxy-1-thio-β-D-galactopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 819798-40-8 phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside 

Downstream Products

• 187022-49-7 (2R,3S,4R,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)-5-(((2,2,2-trichloroethoxy)carbonyl)amino)tetrahydro-2H-pyran-3,4-diyl diacetate 
• 676227-84-2 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-((2R,3R,4R,5R,6S)-5-azido-3-benzyloxy-4-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester 
• 676227-83-1 (2S,3R,4R,5R,6R)-3-Azido-5-benzyloxy-2-phenylsulfanyl-6-triethylsilanyloxymethyl-tetrahydro-pyran-4-ol 

Relevant academic research and scientific papers

An improved method for the synthesis of protected glycosyl fluorides from thioglycosides using N,N-diethylaminosulfur trifluoride (DAST)

The direct conversion of thioglycosides to glycosyl fluorides frequently used in oligosaccharide synthesis was examined using N,N-diethylaminosulfur trifluoride (DAST). Although the reaction proceeded without N-bromosuccinimide (NBS), in some cases it was found that the electrophilicity of the Vilsmeier-type electrophilic sulfinium cation species was not sufficient for the activation of certain less-reactive thioglycosides. Here, we report the results of fluorination reactions of a series of monosaccharides using DAST in the absence of NBS, and also discuss the acceleration of the reaction in the presence of dimethyl(methylthio)sulfonium trifluoromethanesulfonate (DMTST) resulting in excellent product yields.

Efficient synthesis of core 2 class glycosyl amino acids by one-pot glycosylation approach

We describe the one-pot synthesis of core 2 class branched oligosaccharides initiated by chemo-selective glycosylation of silyl ether. Glycosylation of 6-O-silyl-4-benzyl-2-azido-thiogalactoside with glycosyl fluoride provided selectively 6-glycosylated thioglycoside without both O-glycosylation at the 3 position and S-glycosylation. Subsequent coupling of galactosyl fluoride and amino acids afforded the protected branched oligosaccharides in good yields.