1 The Chemistry and Biochemistry of C-Nucleosides and C-Arylglycosides

Hacksell, Uli; Gd, Daves

doi:10.1016/s0079-6468(08)70228-5

Cited by 204 publications

(56 citation statements)

References 288 publications

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“…reaction with the tin glucal 11 are electron-rich aromatic bromides. Thus, the improved yield in the preparation of the anisole derivative 36 (Table 2, entries 15 and 16 (73-81%)) compared with the yield for the preparation of 28 (Table 1, entry 19 (30%)) was gratifying since many of the naturally occurring C-aryl glycosides are oxygen-substituted aromatics (1,2). As expected, there was no evidence for the production of the glucal dimer that previously had been the major by-product (up to 18%) in all of our coupling reactions with stannyl glucal 11.…”

Section: No Pd Catalystmentioning

confidence: 99%

“…The class of natural products known as the C-aryl glycosides (1,2) has recently received a great deal of attention in the synthetic community since many of these compounds exhibit unique antibiotic and (or) antitumor activity. Although the key structural unit that identifies these compounds is the novel carbon-carbon bond that unites the carbohydrate and aromatic fragments, a further subclassification can be made based upon the type of substitution at C1 and C2 of the carbohydrate moiety.…”

Section: Introductionmentioning

confidence: 99%

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The preparation of C-aryl glucals via palladium-catalyzed cross-coupling methods

Friesen¹,

Loo²,

Sturino³

1994

Can. J. Chem.

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. Can. J. Chem. 72, 1262 (I 994).The C-aryl glucals 17-31 have been prepared by the palladium-catalyzed cross coupling of l-tributylstannyl-3,4,6-tri-0-(tert-butyldimethylsily1)-D-glcal (11) and aryl bromides. The major by-product in all of these reactions is the dimer 33, the product of homocoupling of 11. Alternatively, the C-aryl glucals 34-40 can be obtained from the palladium-catalyzed coupling of l-iodo-3,4,6-tri-0-(triisopropylsilyl)-~-glucal (16) and a variety of metalated aromatics, including ArZnC1, ArB(OH),, and ArB(OMe),. The advantages of the latter procedure include superior coupling yields under milder reaction conditions and the high yielding preparation of 16 directly from 3,4,6-tri-0-(triisopropylsily1)-D-glucal (12) by a metalation-iodination sequence.RICHARD W. FRIESEN, RICHARD W. LOO et CLAUDIO F. S m o . Can. J. Chem. 72, 1262Chem. 72, (1994.On a prCparC les C-aryl glucals 17-31 par un couplage croisC catalysC par le palladium du 1-tributylstannyl-3,4,6-tri-0-(tert-butyldimCthylsily1)-D-glucal (11) et des brornures d'aryle. Le sous-produit principal de toutes ces rkactions est le dimkre 33, le produit d'homocouplage du produit 11. On peut aussi obtenir les C-aryl glucals 34-40 par un couplage catalysC par le palladium du 1-iodo-3,4,6-tri-0-(triisopropylsilyl)-~-glucal (16) avec une variktC de produits aromatiques mCtallCs comportant le ArZnC1, le ArB(OH), et ArB(OMe),. Les avantages de la dernikre mCthode incluent des rendements supCrieurs de couplage dans des conditions plus douces et la pr~paration avec un rendement Clevk du composC 16 directement 2 partir du 3,4,6-tri-0-(triisopropylsily1)-D-glucal (12) par une sequence de metallation et d'iodation.[Traduit par la RCdaction]

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Section: No Pd Catalystmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

The preparation of C-aryl glucals via palladium-catalyzed cross-coupling methods

Friesen¹,

Loo²,

Sturino³

1994

Can. J. Chem.

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“…Characteristic structural feature of these compounds is an aromatic moiety directly attached to a carbohydrate via a C-C rather than a C-O bond. C-aryl glycosides are frequently found in the aglycon part of various antitumor antibiotics [54] and as natural products originating from various plants. [55] Consequently, many syntheses have been published and the subject of C-aryl glycoside synthesis has been extensively re-viewed.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 3‐Deoxy Glycals via Tandem Metathesis Sequences and Their Use in an Intermolecular Heck Arylation

Schmidt

Biernat

2008

Eur J Org Chem

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Deoxy glycals can be synthesized from a mannitol-derived C 2 -symmetric diene diol by using the tandem RCM/isomerization approach. Incorporation of a ruthenium-catalyzed dehydrogenative silylation step into the reaction sequence is possible. Thus, an orthogonally protected 3-deoxy glycal results via a tandem RCM/hydrosilylation/isomerization sequence. All ruthenium-catalyzed steps of this tandem se-

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“…[3][4][5][6][7][8][9][10] Indeed, the modern structural features of nucleosides are somewhat different from those present in poly-ribonucleotides RNA and DNA, [11] by means of variations in sugar, heterocyclic moieties and the various modes of attachments between the two major components (sugar and heterocycle). The literature of the new kinds of nucleosides is increasing and a lot of variations and kinds of nucleosides with dinuclear nucleosides [12,13] and others were also reported.…”

Section: Introductionmentioning

confidence: 99%

Computational Study of some Double Headed Acyclo-C-Nucleosides

Amara

Tchouar

Belaidi

2015

ILCPA

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ABSTRACT. In the present paper we have a focus in a study of theoretical characterization of three double headed acyclo-C-nucleosides, which are a recent target of experimental studies. The structural and electronic properties of double headed acyclo-C-nucleosides, 1,4-bis(3-mercapto-1H-1,2,4-triazol-5-yl)butane-1,2,3,4-tetrol, 1,4-bis(4-amino-5-mercapto-4H-1,2,4-triazol-3-yl)butane-1,2,3,4-tetrol and 5,5'-(1,2,3,4-tetrahydroxybutane-1,4-diyl)bis(1,3,4-oxadiazole-2(3H)-thione), have been investigated theoretically by performing semi-empirical molecular orbital, ab initio Hartree-Fock (HF) and Density Functional Theory (DFT) calculations. Geometries of the three molecules are optimized at the level of Austin Model 1 (AM1). The electronic properties and relative energies of the molecules have been calculated by HF and DFT in the ground state.

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1 The Chemistry and Biochemistry of C-Nucleosides and C-Arylglycosides

Cited by 204 publications

References 288 publications

The preparation of C-aryl glucals via palladium-catalyzed cross-coupling methods

The preparation of C-aryl glucals via palladium-catalyzed cross-coupling methods

Synthesis of 3‐Deoxy Glycals via Tandem Metathesis Sequences and Their Use in an Intermolecular Heck Arylation

Computational Study of some Double Headed Acyclo-C-Nucleosides

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