67540-18-5

Basic information

• Product Name: 4'-Methoxyphenyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
• Synonyms: 4'-Methoxyphenyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
• CAS NO: 67540-18-5
• Molecular Weight: 646.78
• Mol File: 67540-18-5.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: 4'-Methoxyphenyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-Methoxyphenyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside(67540-18-5)
• EPA Substance Registry System: 4'-Methoxyphenyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside(67540-18-5)

Safety Data

• Hazardous Substances Data: 67540-18-5(Hazardous Substances Data)

Upstream product

• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 150-76-5 4-methoxy-phenol 
• 78153-79-4 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl fluoride 
• 5720-07-0 4-methoxyphenylboronic acid 
• 4196-35-4 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide 
• 126709-11-3 1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-hydrazi-D-glucitol 
• 138963-17-4 N'-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-4-toluenesulfonohydrazide 
• 138963-18-5 N'-(2,3,4,6-tetra-O-benzyl-D-glucopyranosylidene)-4-toluenesulfonohydrazide 
• 139212-74-1 N-sodio-N'-(2,3,4,6-tetra-O-benzyl-D-glucopyranosylidene)-4-toluenesulfonohydrazidate 
• 84380-06-3 1-O-(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)-4-methoxybenzene 
• 90357-89-4 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl trichloroacetimidate 
• 25320-59-6 tetra-O-benzyl glucopyranosyl chloride 
• 85481-53-4 p-methoxyphenyl α-D-glucopyranoside 
• 100-39-0 benzyl bromide 

Downstream Products

• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 

Relevant articles and documents

C -Glycosylation enabled by N -(glycosyloxy)acetamides

The C-glycosylation of C-nucleophiles including allyltrimethylsilane, silyl enol ethers and phenols with N-(glycosyloxy)acetamides as glycosyl donors has been realized. This protocol provides a convenient and practical route for the synthesis of alkyl C-glycosides and aryl 2-deoxy-β-C-glycosides under mild reaction conditions.

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.

Catalytic glycosylation with rhodium(III)-triphos catalysts

The formation of glycosides in high yield from 1-hydroxy sugars using catalytic amounts (0.5molpercent) of Rh(III)Cl3(triphos) (1a) or [Rh(III)(MeCN)3(triphos)](TfO)3 (1b) is described. High stereocontrol at the anomeric c