Selective benzoylation of diols with 1-(benzoyloxy)benzotriazole

Kim, Sunggak; Chang, Ho-Nam; Kim, Wan Joo

doi:10.1021/jo00210a036

Cited by 92 publications

(42 citation statements)

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“…Synthesis of 2',3'-di-O-acylated uridine derivatives (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14). (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14).…”

Section: Scheme 1 Synthesis Of 5'-o-n-acetylsulfanilyluridine (2)mentioning

confidence: 99%

“…Table 2. Physicochemical properties of the synthesized of uridine derivatives (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14).…”

Section: Scheme 1 Synthesis Of 5'-o-n-acetylsulfanilyluridine (2)mentioning

confidence: 99%

“…The study was found to be very promising since in all the cases, a single monosubstitution product was isolated reasonably high yields. Furthermore, the N-acetylsulfanilyl acylation product was converted into a series of acyl derivatives (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14). These newly synthesized products may be used as important pre-cursors for the modification of the uridine molecule at different positions.…”

Section: Compound No Rt (H) Rf Yield (%) Physical Statementioning

confidence: 99%

“…During the last few years, many workers have investigated selective acylation and alkylation of hydroxyl groups of the carbohydrate moieties of nucleosides and nucleotides using various methods [6]- [8]. Different methods for acylation of carbohydrates and nucleosides have so far been developed and employed successfully [9] [10]. Of these, direct method has been found to be the most encouraging method for acylation of carbohydrates and nucleosides [11].…”

Section: Introductionmentioning

confidence: 99%

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Chemically Modified Uridine Molecules Incorporating Acyl Residues to Enhance Antibacterial and Cytotoxic Activities

Kawsar¹,

Ara²,

Uddin³

et al. 2015

IJOC

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A new N-acetylsulfanilylation series of uridine have been synthesized in good yield using direct acylation method and afforded the 5'-O-N-acetylsulfanilyluridine. In order to obtain newer products, the 5'-O-N-acetylsulfanilyluridine derivative was further transformed to a series of 2',3'-di-Oacyl derivatives containing a wide variety of functionalities in a single molecular framework. The chemical structures of the newly synthesized compounds were confirmed on the basis of their FTIR, 1 H-NMR spectroscopy, physicochemical properties and elemental analysis. All the synthesized uridine derivatives were tested for their in vitro antibacterial activity against six human pathogenic bacterial strains and for comparison standard antibiotic Ampicillin was also determined. The study revealed that the selectively acylated derivatives 5'-O-N-acetylsulfanilyl-2',3'-di-O-lauroyluridine and 5'-O-N-acetylsulfanilyl-2',3'-di-O-pivaloyluridine showed highest inhibition against Staphylococcus aureus and Bacillus cereus, respectively. We also observed that the introduction of hexanoyl, decanoyl, lauroyl, myristoyl and pivaloyl groups, the antibacterial functionality of the compound uridine increases. Another noteworthy observation was that the uridine derivatives * Corresponding author. S. M. A. Kawsar et al. 233were found comparatively more effective against Gram-positive microorganisms than those of Gram-negative microorganisms. In addition, the test chemicals were also tested for cytotoxicity by brine shrimp lethality bioassay and compounds showed different rate mortality with different concentrations.

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“…Synthesis of 2',3'-di-O-acylated uridine derivatives (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14). (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14).…”

Section: Scheme 1 Synthesis Of 5'-o-n-acetylsulfanilyluridine (2)mentioning

confidence: 99%

“…Table 2. Physicochemical properties of the synthesized of uridine derivatives (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14).…”

Section: Scheme 1 Synthesis Of 5'-o-n-acetylsulfanilyluridine (2)mentioning

confidence: 99%

Section: Compound No Rt (H) Rf Yield (%) Physical Statementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Chemically Modified Uridine Molecules Incorporating Acyl Residues to Enhance Antibacterial and Cytotoxic Activities

Kawsar¹,

Ara²,

Uddin³

et al. 2015

IJOC

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“…1 Acyl groups, especially acetyl and benzoyl, are generally used as electron-withdrawing protecting groups to block hydroxyls, and also used as good neighboring participating groups at 2-position for anomeric stereocontrol in glycosylation reactions. Although some selective protection approaches such as the use of 1-(benzoyloxy)benzotriazole (BzOBT), [2][3][4][5] the dibutyltin oxide mediated selective monoprotection strategy, 6,7 the phase-transfer method, 8 the silver(I) oxide promoted acylation technique, 9 the Cu(II)-mediated acylation procedure, 10 or the selective activation of hydroxyl groups through stannylene compounds, 11 as well as enzyme methods 12 are available, these methodologies are mostly focused on the selective acylation of sugar 2,3-or 4,6-diols. Regioselective protection at the anomeric hydroxyl group is, however, a challenge for chemists.…”

Section: Introductionmentioning

confidence: 99%

Regio- and stereoselective anomeric esterification of glucopyranose 1,2-diols and a facile preparation of 2-O-acetylated glucopyranosyl trichloroacetimidates from the corresponding 1,2-diols

Zhang

Liang

Wang

et al. 2007

Carbohydrate Research

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Abstract-A highly regio-and stereoselective anomeric esterification of 3-O-allyl (or benzyl, or benzoyl)-4,6-O-isopropylidene-a,b-D D-glucopyranose with acetyl chloride, or allyl chloroformate, or ethyl chloroformate gave the corresponding 2-OH, 1-b-acetates or -carbonates in excellent yields. The 2-OH, 1-b-acetates were readily converted to the corresponding 2-O-acetylated glucopyranosyl trichloroacetimidates by reaction with trichloroacetonitrile via base promoted acetyl migration, while the 2-OH, 1-b-carbonates were good glycosyl acceptors for the synthesis of (1!2)-linked oligosaccharides.

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Comparison of Bimacrocyclic, Monomacrocyclic, and Nonmacrocyclic Bis(amidomethyl)pyridines as Catalysts in the Base-Catalyzed Addition of Alcohols to Ketenes

Petersen

Lüning²

1999

Eur. J. Org. Chem.

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Nineteen new bimacrocyclic, monomacrocyclic, and nonmacrocyclic pyridines 1–6 bearing amide functions have been synthesized and utilized in base‐catalyzed additions of alcohols (ethanol, 2‐propanol) and polyols [propane‐1,2‐diol (11a), butane‐1,3‐diol (12a), methyl 4,6‐O‐benzylidene‐α‐D‐glucopyranoside (13a)] to diphenylketene. Compounds 4c, 4d and 1b proved to be efficient and selective catalysts; 4c and 4d exhibited better results with 11a and 12a, and 1b was the best catalyst for selective 2‐O‐acylation of 13a.

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Selective benzoylation of diols with 1-(benzoyloxy)benzotriazole

Cited by 92 publications

References 1 publication

Chemically Modified Uridine Molecules Incorporating Acyl Residues to Enhance Antibacterial and Cytotoxic Activities

Chemically Modified Uridine Molecules Incorporating Acyl Residues to Enhance Antibacterial and Cytotoxic Activities

Regio- and stereoselective anomeric esterification of glucopyranose 1,2-diols and a facile preparation of 2-O-acetylated glucopyranosyl trichloroacetimidates from the corresponding 1,2-diols

Comparison of Bimacrocyclic, Monomacrocyclic, and Nonmacrocyclic Bis(amidomethyl)pyridines as Catalysts in the Base-Catalyzed Addition of Alcohols to Ketenes

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