97133-50-1

Upstream product

• 86386-88-1 methyl 2,4-di-O-acetyl-3-O-benzoyl-β-D-xylopyranoside 
• 98-88-4 benzoyl chloride 
• 612-05-5 methyl-β-D-xylopyranoside 
• 74162-08-6 methyl 2,4-di-O-acetyl-β-D-xylopyranoside 
• 91-09-8 methyl β-L-arabinopyranoside 

Downstream Products

• 87461-37-8 Benzoic acid (2R,3R,4S,5R)-2-methoxy-3,5-bis-trimethylsilanyloxy-tetrahydro-pyran-4-yl ester 
• 83175-48-8 methyl 3-O-benzoyl-2,4-di-O-p-tolylsulfonyl-β-D-xylopyranoside 

Relevant academic research and scientific papers

Benzoxaborole Catalyst for Site-Selective Modification of Polyols

The site-selective modification of polyols bearing several hydroxyl groups without the use of protecting groups remains a significant challenge in synthetic chemistry. To address this problem, novel benzoxaborole derivatives were designed as efficient catalysts for the highly site-selective and protecting-group-free modification of polyols. To identify the effective substituent groups enhancing the catalytic activity and selectivity, a series of benzoxaborole catalysts 1a–k were synthesized. In-depth analysis for the substituent effect revealed that 1i–k, bearing multiple electron-withdrawing fluoro- and trifluoromethyl groups, exhibited the greatest catalytic activity and selectivity. Moreover, 1i-catalyzed benzoylation, tosylation, benzylation, and glycosylation of various cis-1,2-diol derivatives proceeded with good yield and site-selective manner.

Catalytic Activation of Cis-Vicinal Diols by Boronic Acids: Site-Selective Acylation of Carbohydrates

Site-selective acylation of unprotected carbohydrates by using stable, storable, and easily handled imidazole-containing organoboronic acid catalysts is described. This catalytic process with low catalyst loading enables the introduction of a wide variety of acyl functional groups into the equatorial position of cis-vicinal diols in unprotected hexapyranosides with excellent site selectivity. This is the first example that uses a Lewis base-containing boronic acid to enhance the nucleophilicity of hydroxy groups.

Reversible covalent interactions of β-aminoboronic acids with carbohydrate derivatives

β-Aminoalkylboronic acids are capable of binding to carbohydrate derivatives through reversible covalent interactions. An anthracene-bearing β-aminoboronic acid has been synthesized, enabling determinations of association constants for binding of sugars b

Borinic acid-catalyzed regioselective acylation of carbohydrate derivatives

Reversible covalent interactions of organoboron compounds are exploited as the basis for regioselective borinic acid-catalyzed acylations of polyols. This catalytic protocol enables differentiation of the secondary OH groups of a wide range of carbohydrat

Regioselective benzoylation of glycopyranosides by benzoyl chloride in the presence of MoO2(acac)2

Benzoylation of methyl and benzyl glycopyranosides by benzoyl chloride in the presence of MoO2(acac)2 as a catalyst resulted in 3-benzoates with good yield and high regioselectivity. Simple synthesis of the monobenzoates of some glyc

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.

13C AND 1H NMR SPECTRA OF ALL METHYL O-BENZOYL-β-D-XYLOPYRANOSIDES. NONADITIVITY OF ACYLATION EFFECTS ON 13C CHEMICAL SHIFTS IN DEUTERIOCHLOROFORM SOLUTIONS

All methyl O-benzoyl-β-D-xylopyranosides have been prepared and their 1H and 13C NMR spectra measured in deuteriochloroform solutions.The 1H NMR spectra were analysed to the first order and assigned with the aid of homonuclear decoupling.The 13C chemical