156407-74-8

Upstream product

• 1194045-30-1 but-2-ynyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside 
• 100-51-6 benzyl alcohol 
• 3866-62-4 2,3,4,6-tetrakis-O-(phenylmethyl)-1-O-acetyl-α-D-galactopyranose 
• 53081-30-4 tetra-O-benzyl-α-D-galactosyl bromide 
• 90358-01-3 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl trichloroacetimidate 
• 211678-08-9 p-methylphenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside 
• 139974-84-8 phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-galactopyranoside 

Relevant academic research and scientific papers

N-benzoylglycine/thiourea cooperative catalyzed stereoselective O-glycosidation: Activation of O-glycosyl trichloroacetimidate donors

A new practical utility for β-stereoselective glycosylation via activation of O-glycosyl trichloroacetimidate donors using N-benzoylglycine/thiourea cooperative catalysis has been demonstrated. This method represents the first instance where amino acid derived N-benzoylglycine is used as a catalyst for O–glycosylation under mild reaction conditions at ambient temperature. NMR spectroscopy studies suggest that thiourea cocatalyst exhibit a cooperative behaviour that has a strong effect on the reaction rate, yield, and the β-selectivity.

Electron-deficient pyridinium salts/thiourea cooperative catalyzed O-glycosylation via activation of O-glycosyl trichloroacetimidate donors

The glycosylation of O-glycosyl trichloroacetimidate donors using a synergistic catalytic system of electron-deficient pyridinium salts/aryl thiourea derivatives at room temperature is demonstrated. The acidity of the adduct formed by the 1, 2-addition of

Metal-free and VOC-free: O -glycosylation in supercritical CO2

Supercritical carbon dioxide (scCO2) is a suitable medium to perform transition metal-free glycosylation reactions in the absence of volatile organic solvents (VOCs) using glycosyl halides as glycosyl donors. The methodology described here can be applied for obtaining O-glycosides in a totally green reaction, as well as orthoesters, depending on the reaction conditions. The process is much more sensitive to temperature changes than to pressure modification, with glycosyl chlorides requiring higher temperatures to be activated than glycosyl bromides. Pivaloyl groups act as good CO2-philic units and are shown to be the best choice to obtain good stereoselectivities. The relevance of the fluid nature and supercritical conditions was also evidenced.

A versatile glycosylation strategy: Via Au(III) catalyzed activation of thioglycoside donors

Among various methods of chemical glycosylations, glycosylation by activation of thioglycoside donors using a thiophilic promoter is an important strategy. Many promoters have been developed for the activation of thioglycosides. However, incompatibility w

[bmim][OTf]: a versatile room temperature glycosylation promoter

[bmim][OTf] is a versatile, ionic liquid promoter for the room temperature glycosylation of both thiophenyl and trichloroacetimidate glycoside donors; the conditions are mild, with no requirement for molecular sieves, and are compatible with a wide range

Glycosylation using unprotected alkynyl donors

(Chemical Equation Presented) Gold(III) activation of unprotected propargyl glycosyl donors has been shown to be effective for the synthesis of saccharides. Terminal propargyl glycosides of glucose, galactose, and mannose required heating at reflux in ace