77667-81-3

Upstream product

• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 135-19-3 β-naphthol 
• 79386-43-9 diphenyl 2,3,4,6-tetra-O-benzyl-α-D-glucosyl phosphate 
• 78153-79-4 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl fluoride 
• 74808-09-6 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate 
• 4196-35-4 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 580-13-2 2-bromonaphthalene 

Relevant academic research and scientific papers

Synthesis of Phenolic Glycosides: Glycosylation of Sugar Lactols with Aryl Bromides via Dual Photoredox/Ni Catalysis

Multifarious sugar lactols were efficiently transformed into the corresponding phenolic glycosides by treating with aryl bromides in acetonitrile with Ir[dF(CF3)ppy]2(dtbbpy)(PF6) as a photocatalyst under visible light irr

Application of silver N-heterocyclic carbene complexes in O-glycosidation reactions

We report the efficient O-glycosidation of glycosyl bromides with therapeutically relevant acceptors facilitated by silver N-heterocyclic carbene (Ag-NHC) complexes. A set of four Ag-NHC complexes was synthesized and evaluated as promoters for glycosidation reactions. Two new bis-Ag-NHC complexes derived from ionic liquids 1-benzyl-3-methyl-1H-imidazolium chloride and 1-(2-methoxyethyl)-3-methylimidazolium chloride were found to efficiently promote glycosidation, whereas known mono-Ag complexes of 1,3-bis(2,4,6- trimethylphenyl)imidazolium chloride and 1,3-bis(2,6-di-isopropylphenyl) imidazolium chloride failed to facilitate the reaction. The structures of the promoters were established by X-ray crystallography and these complexes were employed in the glycosidation of different glycosyl bromide donors with biologically valuable acceptors, such as estrone, estradiol, and various flavones. The products were obtained in yields considered good to excellent, and all reactions were highly selective for the β isomer regardless of neighboring group effects.

Selective formation of β-O-aryl glycosides in the absence of the C(2)-ester neighboring group

(Chemical Equation Presented) The development of a general and practical method for the stereoselective synthesis of β-O-aryl glycosides that exploits the nature of a cationic palladium(II) catalyst, instead of a C(2)-ester directing group, to control the

Metallocene bis(perfluoroalkanesulfonate)s as air-stable cationic Lewis acids

Zirconocene and titanocene bis(perfluorooctanesulfonate)s were synthesized. In contrast to the corresponding triflates and perchlorates, these compounds are air- and water-stable. They were proved to be ionic on the basis of conductivity measurements and X-ray analysis, allowing these complexes to be stored for months. The strong Lewis acidity of these cationic metallocene species, which was proved by ESR study, enabled catalytic glycosylation.

Synthesis of C-Aryl and C-Alkyl Glycosides Using Glycosyl Phosphates

matrix presented Mannosyl and glucosyl phosphate donors were successfully used in constructing C-aryl linkages common to many natural products via a Lewis acid induced Fries-like rearrangement. The rearrangement was stereo- and regiospecific, yielding onl

SYNTHESIS OF PHENYL D-GLUCOPYRANOSIDES; NUCLEOPHILIC SUBSTITUTION OF O-(2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSYL)-PSEUDOUREAS BY PHENOLS

A series of nucleophilic substitution-reactions of O-(2,3,4,6-tetra-O-benzyl-D-glucopyranosil)pseudoureas by phenols was investigated as a novel procedure for the synthesis of phenyl D-glucopyranoside derivatives; these reactions were found to give the corresponding phenyl 2,3,4,6-tetra-O-benzyl-D-glucopyranosides in excellent yields.Reaction mechanisms were discussed on the basis of the results obtained.

α-Glucosylation of Phenols with Tetra-O-benzyl-α-D-glucose

An α-glucosylation of phenols with 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose is described.This uses a mixture of p-nitobenzenesulfonyl chloride, silver trifluoromethanesulfonate and triethylamine in dichloromethane in a two-stage treatment.