50720-98-4

Upstream product

• 130132-24-0 1,2:3,4-di-O-isopropylidene-6-O-(2-phenyl-1,3-benzodithiol-2-yl)-α-D-galactose 
• 126841-29-0 (3aR,5R,5aS,8aS,8bR)-5-(Dibromo-phenyl-methoxymethyl)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran 
• 93-58-3 benzoic acid methyl ester 
• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 98-88-4 benzoyl chloride 
• 58931-11-6 (C₄H₉)3SnOCH₂C₇H₅O₅(CH₃)4 
• 100-52-7 benzaldehyde 
• 1934-92-5 N-methyl-N-phenyl-benzamide 

Downstream Products

• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 138188-87-1 Benzoic acid (2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-fluoro-tetrahydro-pyran-2-ylmethyl ester 

Relevant academic research and scientific papers

Electrochemical glycosylation in the presence of a catalytic chemical mediator

Electrochemical glycosylation of thioglycoside donors proceeds efficiently in an undivided cell in the presence of a catalytic amount of the chemical mediator (4-bromophenyl) ammoniumyl hexachloroantimonate (BAHA). In comparison with electrochemical glyco

Pd-Catalyzed para-selective C-H difluoromethylation of aromatic carbonyls

A novel palladium catalyzed highly para-selective C-H difluoromethylation of electron-deficient aromatic carbonyls was developed. Diverse substituted aromatic ketones and benzoates were selectively difluoromethylated at the remote para-site of carbonyl gr

Conversion of amides to esters by the nickel-catalysed activation of amide C-N bonds

Amides are common functional groups that have been studied for more than a century. They are the key building blocks of proteins and are present in a broad range of other natural and synthetic compounds. Amides are known to be poor electrophiles, which is typically attributed to the resonance stability of the amide bond. Although amides can readily be cleaved by enzymes such as proteases, it is difficult to selectively break the carbon-nitrogen bond of an amide using synthetic chemistry. Here we demonstrate that amide carbon-nitrogen bonds can be activated and cleaved using nickel catalysts. We use this methodology to convert amides to esters, which is a challenging and underdeveloped transformation. The reaction methodology proceeds under exceptionally mild reaction conditions, and avoids the use of a large excess of an alcohol nucleophile. Density functional theory calculations provide insight into the thermodynamics and catalytic cycle of the amide-to-ester transformation. Our results provide a way to harness amide functional groups as synthetic building blocks and are expected to lead to the further use of amides in the construction of carbon-heteroatom or carbon-carbon bonds using non-precious-metal catalysis.

3-(Dimethylamino)-1-propylamine: A cheap and versatile reagent for removal of byproducts in carbohydrate chemistry

Inexpensive 3-(dimethylamino)-1-propylamine (DMAPA) was found to be effective in anomeric deacylation reactions giving 1-O deprotected sugars in high yield as precursors for the formation of imidate glycosyl donors. DMAPA was also found to be useful for removing excess reagents such as benzoyl chloride, tosyl chloride, and 2,2,2-trifluoro-N-phenylacetimidoyl chloride. The deacylation reaction could be conducted in moist THF and did not require chromatographic purification since an acidic wash was sufficient to remove excess reagent and the formed byproduct.

Protecting group and solvent effects in electrochemical glycosylation

An investigation is undertaken into the roles of protecting groups and the solvent in the electrochemical-mediated glycosylation of manno thioglycosides. Herein notable differences are observed between electrochemical and chemical glycosylation. Georg Thi

Acylation of carbohydrates over Al2O3: Preparation of partially and fully acylated carbohydrate derivatives and acetylated glycosyl chlorides

Selective and per-O-acylation of carbohydrate derivatives using acyl chlorides and Al2O3, a solid support reagent, is reported. This protocol does not require the addition of any base or activator. This methodology has been further extended to the selective acylation of carbohydrate diols and the one-pot preparation of acetylated glycosyl chlorides direct from free reducing sugars. The yields obtained in most of the cases are excellent.

Synthesis of benzoyl and dodecanoyl derivatives from protected carbohydrates under focused microwave irradiation

A microwave assisted phase transfer transesterification in basic medium with methyl benzoate was studied for several carbohydrates. Small amounts of DMF were necessary to provide good yields (96-76%) within 15 minutes. This method was extended to the synt

2-PHENYL-1,3-BENZODITHIOLYLIUM TRIFLUOROMETHANESULFONATE: A REAGENT FOR THE CONVERSION OF ALCOHOLS INTO BENZYL ETHERS AND BENZOATES UNDER MILD CONDITIONS.

2-Phenyl-1,3-benzodithiolylium trifluoromethanesulfonate, easily prepared from 1,2-benzenedithiol, converts alcohols into dithioorthoesters and ultimately, benzyl ethers (Bu3SnH) and benzoates (HgO/HBF4).

DIBROMINATION OF BENZYLOXY-GROUPS: GLYCOSYL BROMIDES FROM BENZYL GLYCOSIDES

Bromination of benzyloxy groups in sugar derivatives with bromotrichloromethane and ultraviolet light rapidly gives α-bromobenzyloxy sugars.On further irradiation α,α-dibromobenzyloxy derivatives are formed from benzyl sugar ethers, whereas glycosyl bromides are produced from benzyl furanosides and pyranosides.