77667-80-2

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 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 580-13-2 2-bromonaphthalene 
• 194088-19-2 (2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(prop-2-ynyloxy)tetrahydro-2H-pyran 
• 4196-35-4 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide 

Relevant academic research and scientific papers

An Unexpected FeCl 3/C-Catalyzed β-Stereoselective Glycosylation in the Presence of the C(2)-Benzyl Group

An efficient and completely β-stereoselective glycosylation that did not rely on neighboring group participation is described using 2-20 molpercent FeCl 3 /C as the catalyst and benzylated propargyl glycosides as the donors to reach yields up to 96percent under mild condition. With an octatomic-ring intermediate at the α-face of FeCl 3 /C with alkyne of propargyl glycosides, a panel of aglycones comprising aliphatic, alicyclic, unsaturated alcohols, halogenated alcohols, and phenols with different substitution were examined successfully for the exclusive β-stereoselective glycosylation reaction.

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

Iron(iii) chloride modulated selective 1,2-trans glycosylation based on glycosyl trichloroacetimidate donors and its application in orthogonal glycosylation

The development of a new glycosylation method for efficient stereoselective synthesis of β-gluco- and galactosides from their corresponding armed trichloroacetimidate donors mediated by 10 mole% of FeCl3 has been focused. FeCl3 has a

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.

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.

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

Nucleophilic Substitution of Tetra-O-benzyl-α-D-glucopyranosyl 1-O-Phosphate under Phase-transfer Catalysed Conditions

An efficient conversion of tetra-O-benzyl-α-D-glucopyranosyl 1-O-phosphate into corresponding 1-thiosugar derivatives, O-aryl glycosides and azides have been described.Reactions were performed under Phase-Transfer Catalysed conditions or in a Catalytic-Tw

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.