Synthesis of Purine and Pyrimidine 3‘-Amino-3‘-deoxy- and 3‘-Amino-2‘,3‘-dideoxyxylonucleosides

Garcia-Alles, Luis F.; Magdalena, Julia; Gotor, Vicente

doi:10.1021/jo9606259

Cited by 26 publications

(15 citation statements)

References 31 publications

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“…Treatment of 9-(β-D-arabinofuranosyl)adenine 366 with Ph 3 P and DEAD in 1,4-dioxane/DMF at 70 ˚C followed by treatment of anhydro [133] dO [134] dX [143] dQ [136] dR [137] dS [138] dP [135] dT [139] dU [140] dV [141] dW [142] X = H, OH oxygen is replaced by nitrogen, was synthesized by a route based on stereospecific formation of the azasugar substrates and their subsequent coupling with a suitable nucleic base. Thus, reaction of 2,3-O-isopropylidene-D-glyceraldehyde with pyrrole derivative 372 in the presence of BF 3 ·OEt 2 gave 373, which was converted to 375 by four steps.…”

Section: Miscellaneousmentioning

confidence: 99%

Sugar-Modified Nucleosides in Past 10 Years, A Review

Ichikawa¹,

Kato

2001

CMC

179

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In the search for effective, selective, and nontoxic antiviral and antitumour agents, a variety of strategies have been devised to design nucleoside analogs. These strategies have involved several formal modifications of the naturally occurring nucleosides, especially, alteration of the carbohydrate moiety. Since the naturally occurring purine nucleoside analog oxetanocin A and its derivatives have been found to be effective as anti-HIV-1 and anti-herpes virus agents in 1986, the syntheses of different types of sugar-modified nucleoside analogs have been reported. In this review we will give an overview of the sugar-modified nucleosides synthesized since the late 1990 according to their structural types along with the synthetic routes of some selected nucleosides.

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Section: Miscellaneousmentioning

confidence: 99%

Sugar-Modified Nucleosides in Past 10 Years, A Review

Ichikawa¹,

Kato

2001

CMC

179

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“…The fourth coupler 3d , bearing acetone oxime as activating group, was prepared in a one step reaction starting with glycerol carbonate chloroformate ( 5 ) and acetone oxime. Acetone oxime phenyl carbonate (acetone O ‐[phenyloxy)carbonyl]oxime) has been used for the regioselective modification of nucleotides using Lipase B from Candida antarctica (CALB); hereby the primary hydroxyl group of the saccharide unit was selectively converted to the corresponding phenyl carbonate 19. The synthetic procedure for 3d is comparable to that of 3a and b ; THF served as the solvent and dry triethylamine as acid scavenger.…”

Section: Resultsmentioning

confidence: 99%

“…Acetone oxime phenyl carbonate (acetone O-[phenyloxy)carbonyl]oxime) has been used for the regioselective modification of nucleotides using Lipase B from Candida antarctica (CALB); hereby the primary hydroxyl group of the saccharide unit was selectively converted to the corresponding phenyl carbonate. [19] The synthetic procedure for 3d is comparable to that of 3a and b; THF served as the solvent and dry triethylamine as acid scavenger. In the reaction beside the desired product 3d the tricarbonate 4 was formed and as a consequence relatively low yield (39%) of 3d was obtained.…”

Section: Synthesis Of Bifunctional Couplersmentioning

confidence: 99%

Carbonate Couplers and Functional Cyclic Carbonates from Amino Acids and Glucosamine

Fricke

Keul

Möller

2009

Macro Chemistry & Physics

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On the basis of glycerol carbonate, four coupling reagents 3a‐d were prepared. Their synthesis and characterisation, starting from glycerol carbonate 2, is described. To evaluate the differences in reactivity these couplers were reacted with valine methyl ester and the results were compared with the already known coupler 3a. Reaction conditions influenced the conversion of the couplers 3a‐d containing phenyl, 4‐nitrophenyl, imidazolyl and acetone oxime leaving groups; highest conversion and fastest reaction rates were obtained with 3b. The coupling reagents 3a and b were used for the synthesis of functional carbonate building blocks from amino acid methyl esters and glucosamine.

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“…Among the latter, ammonia, amines, amino alcohols, diamines, and amino acids were used. Hydrazine can be considered as an amine derivative and as such might react in a way similar to that described previously. 11a, Following this procedure, carbazoyl derivatives could be obtained.…”

Section: Resultsmentioning

confidence: 99%

Chemoenzymatic Synthesis of Novel 3‘- and 5‘-Carbazoyl Nucleoside Derivatives. Regioselective Preparation of 3‘- and 5‘-Alkylidencarbazoyl Nucleosides

et al. 1998

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A chemoenzymatic procedure is described for the synthesis of 3‘- and 5‘-carbazoyl nucleoside derivatives 12a,b, 13a,b, 14b,c, and 30b, and these are prepared for the first time. This process involves the regioselective enzymatic alkoxycarbonylation of nucleosides and the subsequent transformation with hydrazine into novel carbazoyl nucleoside derivatives. Taking into account previously reported data (relative to nucleoside, hydrazone, carbazate, and aryloxyphenoxypropionate derivatives), 3‘-alkylidencarbazoyl 2‘-deoxynucleosides 15a,b−18a,b, 5‘-alkylidencarbazoyl 2‘-deoxynucleosides 19a,b−22a,b, 5‘-alkylidencarbazoyl ribonucleosides of uridine 23c−26c, and 5‘-alkylidencarbazoyl-2‘,3‘-isopropylideneadenosine 31b−34b emerge as interesting targets since they combine structural features found in both therapeutic nucleoside derivatives and fungicide/herbicide nucleoside analogues.

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Synthesis of Purine and Pyrimidine 3‘-Amino-3‘-deoxy- and 3‘-Amino-2‘,3‘-dideoxyxylonucleosides

Cited by 26 publications

References 31 publications

Sugar-Modified Nucleosides in Past 10 Years, A Review

Sugar-Modified Nucleosides in Past 10 Years, A Review

Carbonate Couplers and Functional Cyclic Carbonates from Amino Acids and Glucosamine

Chemoenzymatic Synthesis of Novel 3‘- and 5‘-Carbazoyl Nucleoside Derivatives. Regioselective Preparation of 3‘- and 5‘-Alkylidencarbazoyl Nucleosides

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