14315-83-4

Upstream product

• 98-88-4 benzoyl chloride 
• 3396-99-4 methyl α-D-galactopyranoside 
• 93-97-0 benzoic acid anhydride 

Relevant academic research and scientific papers

DBN-Catalyzed Regioselective Acylation of Carbohydrates and Diols in Ethyl Acetate

The 1,5-diazabicyclo[4.3.0]non-5-ene (DBN)-catalyzed regioselective acylation of carbohydrates and diols in ethyl acetate has been developed. The hydroxyl groups can be selectively acylated by the corresponding anhydride in EtOAc in the presence of a catalytic amount (as low as 0.1 equiv.) of DBN at room temperature to 40 °C. This method avoids metal catalysts and toxic solvents, which makes it comparatively green and mild, and it uses less organic base compared with other selective acylation methods. Mechanism studies indicated that DBN could catalyze the selective acylation of hydroxyl moieties through a dual H-bonding interaction.

Regioselective Sulfonylation/Acylation of Carbohydrates Catalyzed by FeCl3 Combined with Benzoyltrifluoroacetone and Its Mechanism Study

A catalytic amount of FeCl3 combined with benzoyl trifluoroacetone (Hbtfa) (FeCl3/Hbtfa = 1/2) was used to catalyze sulfonylation/acylation of diols and polyols using diisopropylethylamine (DIPEA) or potassium carbonate (K2CO3) as a base. The catalytic system exhibited high catalytic activity, leading to excellent isolated yields of sulfonylation/acylation products with high regioselectivities. Mechanism studies indicated that FeCl3 initially formed [Fe(btfa)3] (btfa = benzoyl trifluoroacetonate) with twice the amount of Hbtfa under basic conditions in the solvent acetonitrile at room temperature. Then, Fe(btfa)3 and two hydroxyl groups of the substrates formed a five- or six-membered ring intermediate in the presence of the base. The subsequent reaction between the cyclic intermediate and a sulfonylation reagent led to the selective sulfonylation of the substrate. All key intermediates were captured in the high-resolution mass spectrometry assay, therefore demonstrating this mechanism for the first time.

An inexpensive catalyst, Fe(acac)3, for regio/site-selective acylation of diols and carbohydrates containing a 1,2-: Cis -diol

This work describes the [Fe(acac)3] (acac = acetylacetonate)-catalyzed, regio/site-selective acylation of 1,2- and 1,3-diols and glycosides containing a cis-vicinal diol. The iron(iii) catalysts initially formed cyclic dioxolane-type intermediates with substrates between the iron(iii) species and vicinal diols, and the efficient and selective acylation of one hydroxyl group was subsequently achieved by adding acylation reagents in the presence of diisopropylethylamine (DIPEA) under mild conditions. This reaction generally produced high selectivities and highly isolated yields with the same protection pattern as that achieved with dibutyl tinoxide-mediated schemes.

Diisopropylethylamine-triggered, highly efficient, self-catalyzed regioselective acylation of carbohydrates and diols

A diisopropylethylamine (DIPEA)-triggered, self-catalyzed, regioselective acylation of carbohydrates and diols is presented. The hydroxyl groups can be acylated by the corresponding anhydride in MeCN in the presence of a catalytic amount of DIPEA. This method is comparatively green and mild as it uses less organic base compared with other selective acylation methods. Mechanistic studies indicate that DIPEA reacts with the anhydride to form a carboxylate ion, and then the carboxylate ion could catalyze the selective acylation through a dual H-bonding interaction.

A green and convenient method for regioselective mono and multiple benzoylation of diols and polyols

An efficient method for regioselective benzoylation of diols and polyols was developed. The benzoylation is catalyzed by only 0.2 equiv of benzoate anion in acetonitrile with the addition of a stoichiometric amount of benzoic anhydride under very mild condition, leading to high yields. Compared with all other methods, this method shows particular advantage in regioselective multiple benzoylation of polyols, and in avoiding the use of any metal-based catalysts and any amine bases, which is more environment-friendly.

Regioselective Monoacylation of Some Glycopyranosides via Cyclic Tin Intermediates

Selective mono-benzoylation of some pento- and hexo-pyranosides (Me β-L-Ara, Ph α-L-Ara, Me α-D-Xyl, Me β-D-Xyl, Me α-D-Glc, Me-β-D-Glc, Me α-D-Gal, Me β-D-Gal, and Me α-D-Man) by using Bu2SnO was examined in comparaison with the results of the (Bu3Sn)2O method and direct benzoylation.The Bu2SnO method is particularly useful in that it selectively activates an equatorial hydroxyl group wich bears an oxygenated function (OH or OMe) in a cis relationship at an adjacent position, even in the presence of a more reactive primary OH group.The various mono- and di-O-benzoyl derivatives prepared in this work were unambiguously identified by analysis of their 13C-nuclear magnetic resonance spectra.

REGIOSELECTIVE STANNYLATION. ACYLATION OF CARBOHYDRATES: COORDINATION CONTROL

An efficient method for the regioselective enhancement of the nucleophilicity of polyhydroxy compounds has been developed.Partial stannylation of carbohydrate with (Bu3Sn)2O and subsequent electrophilic attack with benzoyl chloride gave rise to regioselec