Preparation and Synthetic Utility of Some Organotin Derivatives of nucleosides

Wagner, Daniel; Verheyden, Julien P. H.; Moffatt, J. G.

doi:10.1021/jo00915a005

Cited by 293 publications

(101 citation statements)

References 9 publications

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“…Similar reaction and purification procedure was applied to prepare compound 4 (pentanoyl derivative, (CHCl 3 -nC 6 (14) …”

Section: General Procedures For the Synthesis Of Methyl 6-o-myristoyl-mentioning

confidence: 99%

“…Protection of a particular functional group of an organic compound is not only necessary for the modification of properties of the remaining functional groups but also for the synthesis of newer derivatives of great importance. Various methods for acylation of carbohydrates and nucleosides have so far been developed and employed successfully [4][5][6][7][8]. Of these, the direct acylation method is considered as one of the most effective [8,9] for selective acylation of carbohydrates.…”

Section: Introductionmentioning

confidence: 99%

“…The IR spectrum of this compound showed the absorption peaks at 1728, 1690 due to -CO stretching. The 1 H-NMR spectrum of compound 5 displayed two six-proton multiplet at δ 2.26 {3×CH 3 (CH 2 ) 3 CH 2 CO-}, and δ 1.51 {3×(CH 3 ) 2 CH 2 CH 2 CO-}, a twelve-proton multiplet at δ 1.24 {3×CH 3 (CH 2 ) 2 CH 2 CH 2 CO-} and one nine-proton multiplet at δ 0.84 {3×CH 3 (CH 2 ) 4 The same myristoyl derivative 2 was then converted to the octanoyl derivative (6). Its IR spectrum displayed the absorption band at 1712 cm -1 (for -CO).…”

mentioning

confidence: 99%

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Infrared, <sup>1</sup>H-NMR Spectral Studies of some Methyl 6-O-Myristoyl-α-D-Glucopyranoside Derivatives: Assessment of Antimicrobial Effects

Kawsar

Mymona

Asma

et al. 2015

ILCPA

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ABSTRACT.This study was carried out to regioselective myristoylation of methyl α-Dglucopyranoside (1) using the direct acylation method gave the corresponding methyl 6-Omyristoyl-α-D-glucopyranoside (2) in fair yield. A number of 2,3,4-tri-O-acyl derivatives (3-15) of this 6-O-substitution product using a wide variety of acylating agents were also prepared in order to obtain newer derivatives of synthetic and biological importance. The reaction conditions are reasonably simple and yields were very good. The structures of the title compounds (2-15) were established by using analytical, physicochemical techniques and spectroscopic data (IR and 1 H-NMR). All the synthesized compounds were employed as test chemicals for in vitro antimicrobial functionality test against Gram-positive Bacillus subtilis, Staphylococcus aureus, Gram-negative Escherichia coli, Pseudomonas aeruginosa bacteria and plant pathogenic fungi Aspergillus niger and Candida albicans. For comparative studies, antimicrobial activity of standard antibiotics, Ampicillin and Nystatin were also carried out against these microorganisms. The study revealed that the tested samples exhibited moderate to good antibacterial and antifungal activities. It was also observed that the test substances were more effective against fungal phytopathogens than those of the human bacterial strains. Encouragingly, a number of tested chemicals showed nearest antibacterial and antifungal activities with the standard antibiotics employed.

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“…Similar reaction and purification procedure was applied to prepare compound 4 (pentanoyl derivative, (CHCl 3 -nC 6 (14) …”

Section: General Procedures For the Synthesis Of Methyl 6-o-myristoyl-mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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Infrared, <sup>1</sup>H-NMR Spectral Studies of some Methyl 6-O-Myristoyl-α-D-Glucopyranoside Derivatives: Assessment of Antimicrobial Effects

Kawsar

Mymona

Asma

et al. 2015

ILCPA

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“…Melting points were determined on an electro-thermal melting point apparatus (England) and are uncorrected. Evaporations were carried out under reduced pressure using VV-1 type vacuum rotary evaporator (Germany) with a bath temperature below 40 o C. 1 H-NMR spectra (300 MHz) were recorded for solutions in deuteriochloroform (CDCl 3 ) (internal Me 4 Si) with a Bruker DPX-40C spectrometer. Thin layer chromatography (t.l.c) was performed on Kieselgel GF 254 and spots were detected by spraying the plates with 1% H 2 SO 4 and heating at 150-200 o C until coloration took place.…”

Section: Methodsmentioning

confidence: 99%

“…Carbohydrate chemists consider selective acylation as one of the most important and fundamental methods for protection of the hydroxyl groups. A number of methods for selective acylation of carbohydrates have so far been developed and successfully employed [1][2][3][4] . Of these, the direct method is considered as one of the most effective 4 for selective acylation of carbohydrates.…”

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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Di-n-butyltin Oxide

RajanBabu

Otera²

2005

Encyclopedia of Reagents for Organic Synthesis

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Preparation and Synthetic Utility of Some Organotin Derivatives of nucleosides

Cited by 293 publications

References 9 publications

Infrared, <sup>1</sup>H-NMR Spectral Studies of some Methyl 6-O-Myristoyl-α-D-Glucopyranoside Derivatives: Assessment of Antimicrobial Effects

Infrared, <sup>1</sup>H-NMR Spectral Studies of some Methyl 6-O-Myristoyl-α-D-Glucopyranoside Derivatives: Assessment of Antimicrobial Effects

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

Di-n-butyltin Oxide

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