51885-06-4

Upstream product

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

Relevant academic research and scientific papers

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.

Applications of Shoda's reagent (DMC) and analogues for activation of the anomeric centre of unprotected carbohydrates

2-Chloro-1,3-dimethylimidazolinium chloride (DMC, herein also referred to as Shoda's reagent) and its derivatives are useful for numerous synthetic transformations in which the anomeric centre of unprotected reducing sugars is selectively activated in aqueous solution. As such unprotected sugars can undergo anomeric substitution with a range of added nucleophiles, providing highly efficient routes to a range of glycosides and glycoconjugates without the need for traditional protecting group manipulations. This mini-review summarizes the development of DMC and some of its derivatives/analogues, and highlights recent applications for protecting group-free synthesis.

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.