205590-22-3

Basic information

• Product Name: phenyl β-D-glucopyranosyl-(1→3)-1-thio-β-D-glucopyranoside
• Synonyms: phenyl β-D-glucopyranosyl-(1→3)-1-thio-β-D-glucopyranoside
• CAS NO: 205590-22-3
• Molecular Weight: 434.464
• Mol File: 205590-22-3.mol

Chemical Properties

• CAS DataBase Reference: phenyl β-D-glucopyranosyl-(1→3)-1-thio-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl β-D-glucopyranosyl-(1→3)-1-thio-β-D-glucopyranoside(205590-22-3)
• EPA Substance Registry System: phenyl β-D-glucopyranosyl-(1→3)-1-thio-β-D-glucopyranoside(205590-22-3)

Safety Data

• Hazardous Substances Data: 205590-22-3(Hazardous Substances Data)

Upstream product

• 4551-15-9 phenylthiotrimethylsilane 
• 22551-65-1 laminarabiose octaacetate 
• 2936-70-1 (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 2106-10-7 1-deoxy-1-fluoro-α-D-glucose 
• 439-03-2 2,3,4,6-tetra-O-acetyl-1-fluoro-α-D-glucopyranose 
• 83-87-4 D-glucose pentaacetate 
• 13992-16-0 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 108-98-5 thiophenol 
• 604-69-3 β-D-glucose pentaacetate 
• 205590-21-2 phenyl 2,4,6,2',3',4',6'-hepta-O-acetyl-1-thio-β-laminaribioside 

Downstream Products

• 205590-23-4 C₃₉H₃₈O₁₀S 

Relevant articles and documents

Glycosynthase with broad substrate specificity-an efficient biocatalyst for the construction of oligosaccharide library

A versatile glycosynthase (TnG-E338A) with strikingly broad substrate scope has been developed from Thermus nonproteolyticus β-glycosidase (TnG) by using site-directed mutagenesis. The practical utility of this biocatalyst has been demonstrated by the facile generation of a small library containing various oligosaccharides and a steroidal glycoside (total 25 compounds) in up to 100 % isolated yield. Moreover, an array of eight gluco-oligosaccharides has been readily synthesized by the enzyme in a one-pot, parallel reaction, which highlights its potential in the combinatorial construction of a carbohydrate library that will assist glycomic and glycotherapeutic research. Significantly, the enzyme provides a means by which glycosynthase technology may be extended to combinatorial chemistry.

Interglycosidic Acetals IV. Preparation and Regioselective Cleavage of Phenyl 2,2′ : 4,6:4′,6′-Tri-O-benzylidene-l-thio-β-laminaribiosides

A (+)-10-Camphorsulfonic acid-catalysed acetal exchange reaction of phenyl 1-thio-β-laminaribioside using 3.5 molar equivalents of α,α-dimethoxytoluene gave a tris(benzylidene acetal), which was isolated and characterized as phenyl 3′-O-acetyl-2,2′ 4,6:4′6′-tri-O-benzylidene-1-thio-β-laminaribioside, and the corresponding 3′-O-benzyl derivative 6. Upon a treatment with pyridinium p-toluenesulfonate, the interglycosidic 2,2′-acetal in 6 underwent selective cleavage to give the 2,2′-diol. Additionally, a reductive ring-opening reaction of 6 with lithium aluminium hydride/anhydrous aluminium chloride, followed by O-acetylation, gave the 2,6,6′-O-acetyl-4,2',3',4'-tetra-0-benzyl derivative in 73% yield. A different regioselectivity was observed in the reduction of 6 with borane-trimethylamine adduct/anhydrous aluminium chloride or sodium cyanotrihydroborate/methanesulfonic acid, giving the corresponding 2,4,4′-triol as the major product.