Regioselective monoacylation of some glycopyranosides via cyclic tin intermediates.

Tsuda, Yoshisuke; Haque, Md.Eramul; Yoshimoto, Kimihiro

doi:10.1248/cpb.31.1612

Cited by 92 publications

(38 citation statements)

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“…Of the methods used for selective acylation, the direct method was found to be more encouraging (Kabir et al, 2005a). Carbohydrates isolated from natural sources, acyl glycoses and acyl glycosides have immense importance and some of them have effective biological activity (Tsuda et al, 1983). The acyl derivatives of carbohydrates are essential for the synthesis of various natural products and also have great synthetic importance because the products thus obtained may further be utilized as versatile intermediates for the synthesis of higher carbon sugars and other carbohydrate derivatives (Tiwari and Mishra, 2011;Miljkovic, 2009).…”

Section: Introductionmentioning

confidence: 99%

Acylation of D-Glucose Derivatives over C5H5N: Spectral Characterization and in vitro Antibacterial Activities

Kawsar¹,

Uddin²,

Manchur³

et al. 2015

International J. of Biological Chemistry

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Methyl α-D-glucopyranoside was easily prepared by the treatment of D-glucose with anhydrous methyl alcohol in presence of hydrogen chloride at freezing temperature in good yield. Then N-acetylsulfanilylation of methyl α-D-glucopyranoside has been carried out by the direct method and afforded the 6-O-N-acetylsulfanilyl derivative in an excellent yield. In order to obtain newer products, the 6-O-N-acetylsulfanilyl derivative was further transformed to a series of 2,3,4-tri-O-acyl derivatives containing a wide variety of functionalities in a single molecular framework. The chemical structures of the newly synthesized compounds were elucidated by Fourier Transform Infrared spectroscopy (FTIR), 1 H-NMR (Proton nuclear magnetic resonance) spectroscopy elemental and physicochemical properties analysis. All the newly synthesized D-glucose derivatives were tested for their in vitro antibacterial activity against some human pathogenic bacterial strains. The study revealed that a good number of acylated products exhibited promising antibacterial activities. It is expected that the acylated derivatives of D-glucose may be considered as a potential source for developing new and better antibacterial agents against a number of pathogenic organism.

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Section: Introductionmentioning

confidence: 99%

Acylation of D-Glucose Derivatives over C5H5N: Spectral Characterization and in vitro Antibacterial Activities

Kawsar¹,

Uddin²,

Manchur³

et al. 2015

International J. of Biological Chemistry

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“…The 2-O-4-t-butylbenzoyl 2 and its 3-O-acyl derivatives (3)(4)(5)(6)(7)(8)(9)(10)(11)(12) were employed as test chemicals for antibacterial and antifungal screening studies against a number of human pathogenic bacteria and plant pathogenic fungi and the results will be reported later.…”

Section: Resultsmentioning

confidence: 99%

“…Of these, the direct method is considered as one of the most effective 4 for selective acylation of carbohydrates. Of the carbohydrates isolated from natural sources, acyl glycoses and acyl glycosides have immense importance and some of them have effective biological activity 5 . It was found from the literature survey that N, S and X-containing heterocyclic compounds showed marked antimicrobial activities 6 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis And Characterization Of Methyl 4, 6-O-Enzylidene- ?-D-Glucopyranoside Derivatives

Kawsar

Kabir

Bhuiyan

et al. 2013

J. Bangla. Chem. Soc.

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Regioselective benzoylation of methyl 4,6-O-benzylidene-α-D-glucopyranoside (1) using direct acylation method furnished the methyl 4,6-O-benzylidene-2-O-(4-t-butylbenzoyl)-α-D-glucopyranoside (2) in an excellent yield. In order to obtain newer products for antimicrobial screening studies, the 2-O-4-t-butylbenzoyl derivative was further transformed to a series of 3-O-acyl derivatives (2-12) containing a wide variety of functionalities in a single molecular framework.

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“…Other methods for regioselective synthesis include phenylborate esters 6 , isopropylidene acetals 4,7,8 , butane--2,3--diacetals 9,10 , cyclohexylidene acetals 4,11,12 , tin acetals 13 and enzymatic deacetylation 14 . However, most of these methods…”

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confidence: 99%

Tetraisopropyldisiloxane-1,3-diyl as a versatile protecting group for pentopyranosides

Johnsson

2012

Carbohydrate Research

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The protecting group tetraisopropyldisiloxane-1,3-yl has been investigated for simultaneous protection of two hydroxyls on pentopyranosides. Methyl α-Dxylopyranoside is protected in excellent regioselectivity and high yield to form the 2,3-protected xylopyranoside whereas methyl β-D-xylopyranoside gives the 3,4-protected product also with excellent regioselectivity.Pentopyranosides have recently received attention in medicinal chemistry and for example, simple xylosides have shown to be interesting in cancer therapeutics.

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Regioselective monoacylation of some glycopyranosides via cyclic tin intermediates.

Cited by 92 publications

References 0 publications

Acylation of D-Glucose Derivatives over C5H5N: Spectral Characterization and in vitro Antibacterial Activities

Acylation of D-Glucose Derivatives over C5H5N: Spectral Characterization and in vitro Antibacterial Activities

Synthesis And Characterization Of Methyl 4, 6-O-Enzylidene- ?-D-Glucopyranoside Derivatives

Tetraisopropyldisiloxane-1,3-diyl as a versatile protecting group for pentopyranosides

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