51885-06-4

Basic information

• Product Name: p-aminophenyl 1-thio-α-D-mannopyranoside
• Synonyms: p-aminophenyl 1-thio-α-D-mannopyranoside
• CAS NO: 51885-06-4
• Molecular Weight: 287.337
• Mol File: 51885-06-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: p-aminophenyl 1-thio-α-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: p-aminophenyl 1-thio-α-D-mannopyranoside(51885-06-4)
• EPA Substance Registry System: p-aminophenyl 1-thio-α-D-mannopyranoside(51885-06-4)

Safety Data

• Hazardous Substances Data: 51885-06-4(Hazardous Substances Data)

Upstream product

• 530-26-7 D-Mannose 
• 1193-02-8 4-aminotiophenol 
• 51885-03-1 p-nitrophenyl 1-thio-α-D-mannopyranoside 

Relevant articles and documents

Protecting-group-free synthesis of glycopolymers bearing thioglycosides via one-pot monomer synthesis from free saccharides

Polyacrylamides having pendant thioglycosides were successfully synthesized from thioglycosidic monomers that were readily prepared by one-pot method without any protection of the hydroxy groups on the starting free saccharides. The glycomonomers were synthesized by the direct synthesis of thioglycosides using 2-chloro-1,3-dimethylimidazolinium chloride and 4-aminobenzentiol, and the following acrylamidation. They were co-polymerized with acrylamide into glycopolymers by reversible addition-fragmentation chain transfer polymerization using a trithiocarbonate derivative as a chain transfer agent. The gold nanoparticles and gold-coated quartz crystal microbalance sensor immobilized with the thiol-terminated glycopolymers exhibited high affinity for the corresponding lectins due to multivalent interaction between saccharides and protein in aqueous solution.

INSULIN-LIKE, AND INSULIN-ANTAGONISTIC, CARBOHYDRATE DERIVATIVES. THE SYNTHESIS OF ARYL AND ARALKYL D-MANNOPYRANOSIDES AND 1-THIO-D-MANNOPYRANOSIDES

A number of novel, aryl and aralkyl D-mannopyranosides and 1-thio-D-mannopyranosides were synthesized for evaluation of insulin-like and insulin-antagonistic properties.The substituted-phenyl α-D-mannopyranosides were prepared by the general procedure of Helferich and Schmitz-Hillebrecht, the substituted-phenyl 1-thio-α-D-mannopyranosides by a method corresponding to the Michael synthesis of aromatic glycosides, and the aralkyl 1-thio-α-D-mannopyranosides by aralkylation of 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranose 15 and subsequent O-deacetylation.Compound (15) was obtained by basic cleavage of the amidino group in 2-S-(tetra)-O-acetyl-α-D-mannopyranosyl)-2-thiopseudourea hydrobromide, the product of the reaction of tetra-O-acetyl-α-D-mannosyl bromide with thiourea.Benzyl 1-thio-β-D-mannopyranoside, obtained by reaction of the sodium salt of 1-thio-β-D-mannopyranose with α-bromotoluene, and benzyl 1-thio-α-L-mannopyranoside were also synthesized, in order to asses the stereospecificity of the biological activites measured.