Einfache neue Synthese von <i>N</i><sup>6</sup>‐substituierten Adenosinen und 2‐Amino‐adenosinen

Vorbrüggen, Helmut

doi:10.1002/ange.19720840808

Cited by 8 publications

(2 citation statements)

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“…The synthesis of polymers 1a − 1c starts with the corresponding telechelic hydroxyterminated PIB−OH ( 2 ) ( M n = 2500 (PD = 1.17)), prepared by cationic polymerization according to ref c) (Scheme ). Initial attempts to use direct nucleophilic substitution reactions with silylated nucleobases (Vorbrüggen method on halo-terminated PIB) were not successful because of the limited solubility of PIB in dipolar aprotic solvents. We therefore changed our synthetic strategy to the more activated chloromethyl ethers which are more prone to nucleophilic reactivity toward nucleobases such as thymine, uracil, and cytosine .…”

Section: Resultsmentioning

confidence: 99%

“…2,6-Diaminopyridine was recrystallized from boiling chloroform. Silylated nucleobases were prepared according to Griengl et al24a 1- tert -Butyl-3,5-bis(1-chloro-1-methylethyl)benzene (DCCl) was obtained according to Faust et al21e N -(6-Aminopyridine-2-yl)butyramide was obtained according to Lehn et al DMA ( N , N -dimethylacetamide) was dried over calcium hydride and distilled in vacuo before use. n -Hexane was refluxed over concentrated H 2 SO 4 for 48 h in order to remove olefins.…”

Section: Methodsmentioning

confidence: 99%

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Synthesis and Analysis of Telechelic Polyisobutylenes for Hydrogen-Bonded Supramolecular Pseudo-Block Copolymers

et al. 2004

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New telechelic polyisobutylenes (PIB) with hydrogen-bonding motifs were prepared. Nucleobases such as thymine, uracil, and cytosine as well as chelate-type hydrogen-bonding donoracceptors were affixed onto the end groups of the PIB. Starting with PIB of defined molecular weight, prepared by living cationic polymerization, hydroxyterminated PIB was generated, which subsequently was transformed into the corresponding chloromethyl ether. Reaction with silylated nucleobases furnished the final nucleobase-telechelic PIB in high yields. The chelate-type PIB was prepared by a sequence of nucleophilic/addition reaction steps adapted to the low solubility of PIB polymers in polar solvents. The structure of the PIB polymers was proven by 1 H NMR, 13 C NMR, and MALDI-TOF MS analysis proving the complete conversion between the reaction steps in quantitative yields. The pure PIB polymers with specific hydrogen bonding patterns will allow the investigation of supramolecular pseudo-block copolymers.

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Section: Resultsmentioning

confidence: 99%