67525-68-2

Upstream product

• 6689-38-9 (4-methoxyphenoxy)trimethylsilane 
• 89825-08-1 2,3,4,6-tetra-O-benzyl-1-O-trimethylsilyl-α,β-D-glucopyranose 
• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 150-76-5 4-methoxy-phenol 
• 74808-09-6 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate 
• 126709-14-6 1-Azi-2,3,4,6-tetra-O-benzyl-1-deoxy-D-glucopyranose 
• 139212-74-1 N-sodio-N'-(2,3,4,6-tetra-O-benzyl-D-glucopyranosylidene)-4-toluenesulfonohydrazidate 
• 138963-18-5 N'-(2,3,4,6-tetra-O-benzyl-D-glucopyranosylidene)-4-toluenesulfonohydrazide 
• 96863-21-7 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl dimethylphosphinothioate 
• 25320-59-6 tetra-O-benzyl glucopyranosyl chloride 
• 90357-89-4 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl trichloroacetimidate 
• 100-39-0 benzyl bromide 
• 3150-20-7 4-methoxyphenyl β-D-glucopyranoside 
• 2872-65-3 p-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 

Downstream Products

• 4356-78-9 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl chloride 
• 25320-59-6 tetra-O-benzyl glucopyranosyl chloride 
• 1200-06-2 4-methoxyphenyl acetate 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 61474-61-1 methyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)-α-D-glucopyranoside 
• 1206803-42-0 p-methoxyphenyl 2,3,4-tri-O-benzyl-6-O-triethyl-silyl-β-D-glucopyranoside 

Relevant academic research and scientific papers

Stereoselective O-Glycosylations by Pyrylium Salt Organocatalysis**

Despite many years of invention, the field of carbohydrate chemistry remains rather inaccessible to non-specialists, which limits the scientific impact and reach of the discoveries made in the field. Aiming to increase the availability of stereoselective

Visible-light-promoted 3,5-dimethoxyphenyl glycoside activation and glycosylation

A new glycosylation method promoted by visible light with 3,5-dimethoxyphenyl glycoside as the donor was developed. This protocol delivers bothO-glycosides andN-glycosides in moderate to excellent yields using a wide range ofO-nucleophiles and nucleobases as the glycosyl acceptors.

Synthesis of nature product kinsenoside analogues with anti-inflammatory activity

Kinsenoside is the major bioactive component from herbal medicine with a broad range of pharmacological functions. Goodyeroside A, an epimer of kinsenoside, remains less explored. In this report we chemically synthesized kinsenoside, goodyeroside A and their analogues with glycan variation, chirality inversion at chiral center(s), and bioisosteric replacement of lactone with lactam. Among these compounds, goodyeroside A and its mannosyl counterpart demonstrated superior anti-inflammatory efficacy. Furthermore, goodyeroside A was found to suppresses inflammatory through inhibiting NF-κB signal pathway, effectively. Structure-activity relationship is also explored for further development of more promising kinsenoside analogues as drug candidates.

Copper-mediated O-arylation of lactols with aryl boronic acids

An efficient and novel methodology to access phenolic glycosides has been established by using copper-mediated coupling reaction of aryl boronic acids with hemiacetals. The reaction takes place normally in the presence of Cu(OAc)2 (1.0 equiv.) and pyridine (2.0 equiv.) at 40 °C. This protocol distinguishes itself by wide substrate scope, operational simplicity and giving rise to a myriad of phenolic glycosides in good to excellent yields.

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.

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

O-Glycoside Synthesis under Neutral Conditions in Concentrated Solutions of LiClO4 in Organic Solvents Employing Benzyl-Protected Glycosyl Donors

The benzyl-protectd glucosyl trichloroacetimidates, phosphates, and halides 1 are activated under neutral conditions and without the addition of any further promoter in 1 M solutions of LiCl4 in ether, CH2Cl2, CHCl3, or CH3CN and react under these conditi

Conversion of p-methoxyphenyl glycosides into the corresponding glycosyl chlorides and bromides, and into thiophenyl glycosides

p-Methoxyphenyl (pMP) β-D-glycopyranosides (Glc, Gal, GlcNPhth, GalNPhth, GlcNTroc, Galβ4Glc, Galα4Gal) were prepared from the corresponding 1-O-acetyl sugars in 79-90% yield, using boron trifluoride etherate as promoter. Treatment of the pMP glycosides with acyl chlorides or bromides in the presence of various Lewis acids gave the corresponding glycosyl chlorides and bromides in 81-98% yield. Treatment of the acyl-protected pMP glycosides with thiophenol and boron trifluoride etherate gave the corresponding thioglycosides in 80-100% yield and high (> 20:1) β/α selectivity. The stability of pMP glycosides was investigated against a series of reagents.