83135-13-1

Upstream product

• 1928-76-3 9-benzyl-6-chloro-9H-purine 
• 1258274-71-3 9-benzyl-6-iodo-7,8-dihydropurine 
• 100-39-0 benzyl bromide 
• 2545-26-8 6-iodo-7H-purine 
• 87-42-3 6-chloropurine 
• 100-44-7 benzyl chloride 
• 66224-66-6 adenine 
• 4261-14-7 9-benzyl-9H-purin-6-ylamine 
• 2545-26-8 6-iodopurine 
• 100-51-6 benzyl alcohol 

Downstream Products

• 160516-02-9 9-benzyl-6-vinyl-9H-purine 
• 83135-02-8 9-benzyl-6-phenyl-9H-purine 
• 450368-40-8 (E)-1,2-bis(9-benzylpurin-6-yl)ethene 
• 629604-05-3 6-(hydroxymethyl)-9-benzylpurine 
• 773133-82-7 6-(acetyloxymethyl)-9-benzylpurine 
• 773133-70-3 9-benzyl-6-(pivaloyloxymethyl)purine 
• 773133-76-9 6-(benzoyloxymethyl)-9-benzylpurine 

Relevant academic research and scientific papers

Cross-coupling reaction of saccharide-based alkenyl boronic acids with aryl halides: The synthesis of bergenin

A convenient synthetic pathway enabling D-glucal and D-galactal pinacol boronates to be prepared in good isolated yields was achieved. Both pinacol boronates were tested in a series of cross-coupling reactions under Suzuki-Miyaura cross-coupling conditions to obtain the corresponding aryl, heteroaryl, and alkenyl derivatives in high isolated yields. This methodology was applied to the formal synthesis of the glucopyranoside moiety of papulacandin D and the first total synthesis of bergenin. Building blocks with boron: A convenient synthetic route to D-glucal and D-galactal pinacol boronates was developed, and the boronates were used in cross-coupling reactions to generate the corresponding aryl, heteroaryl, and alkenyl derivatives in high yields (see scheme). This methodology was applied to the formal synthesis of the glucopyranoside moiety of papulacandin D and the total synthesis of bergenin.

Selective synthesis of 7-substituted purines via 7,8-dihydropurines

A simple and efficient protocol for the preparation of 7-substituted purines is described. 6- and 2,6-Dihalopurines were N9-tritylated and then transformed to 7,8-dihydropurines by DIBAL-H. Subsequent N 7-alkylation followed by N9-trityl deprotection with trifluoroacetic acid was accompanied by spontaneous reoxidation, which led to the 7-substituted purines at 55 - 88% overall isolated yields.

Synthesis of a cyclic tetrameric purine by successive cross-coupling reactions and subsequent Pd-catalyzed cyclization

The tetrameric N-benzyl-protected purine (quaterpurine) 2 was synthesized and characterized as its palladium complex [2Pd]. The synthesis commenced with the Pd-catalyzed cross-coupling of 8-zincated 9-benzyl-6-chloro-8- iodopurine (9) and 9-benzyl-6-iodopurine (11) establishing the first C-6/ C-8 bond. The sequence was repeated twice after iodo-dechlorination at C-6′ (C-6″) of the respective dimer 12 and trimer 15. The final ring closure was achieved at the tetrameric 6?-chloro-8-iodoquaterpurine 3b by a reductive intramolecular cross-coupling with hexamethylditin in the presence of Pd2(dba)3 and P(2-furyl)3. The overall yield in the eight step sequence was 17 % starting from 9-benzyl-6-chloropurine (8), the immediate precursor of 11. Other strategies to combine the purine fragments, i.e. by dimer/dimer bond formation or by regioselective cross-coupling, were not successful. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

DIKETO ACIDS WITH NUCLEOBASE SCAFFOLDS: ANTI-HIV REPLICATION INHIBITORS TARGETED AT HIV INTEGRASE IN COMBINATION THERAPY

A new class of diketo acids constructed on nucleobase scaffolds, designed as inhibitors of HIV replication through inhibition of HIV integrase, is described. These compounds are useful in the prevention or treatment of infection by HFV and in the treatmen

Diketo acids with nucleobase scaffolds: anti-HIV replication inhibitors targeted at HIV integrase

A new class of diketo acids constructed on nucleobase scaffolds, designed as inhibitors of HIV replication through inhibition of HIV integrase, is described. These compounds are useful in the prevention or treatment of infection by HIV and in the treatmen

Diketo acids on nucleobase scaffolds as inhibitors of Flaviviridae

A new class of diketo acids constructed on nucleobase scaffolds, designed as inhibitors of HCV replication through inhibition of HCV NS5B RNA polymerase, is described. These compounds are useful in the prevention or treatment of infection by HCV and in th

4-Metalated condensed pyrimidines: Their preparation and reaction with aldehydes under barbier-type conditions

Equation presented. The organometallic intermediate obtained from halogen-metal exchanges of 4-iodo-6-phenylthieno[2,3-d]pyrimidine under Barbier-type conditions was reacted with aldehydes to form the corresponding alcohols in moderate yields. The reaction involving an organolithium intermediate proceeded only at low temperature, whereas the reaction involving a magnesium ate intermediate also proceeded at room temperature. A crystal structure confirms that the expected constitutional alcohol isomer is formed, where no migration has taken place. The conditions were also suitable for 9-benzyl-6-iodopurine.

Mitsunobu reactions for the synthesis of carbocyclic analogues of nucleosides: Examintion of the regioselectivity

In order to provide a general synthetic method for carbocyclic nucleosides, regioselectivities in Mitsunobu reaction of purine, pyrimidin-2-one and their substituted derivatives with a variety of alcohols with a variety of alcohols were examined and found to depend upon both substituents of the bases and kind of the alcohols.

Coupling of Diazopurines, a Curious Steric Effect in a Free Radical Reaction

The reaction of adenine derivatives with nitrite esters in the presence of arenes was examined and found to give 6-arylpurines in good (83percent) to poor (11percent) yield.The arylated products consisted only of the meta and para isomers; none of the anticipated ortho isomers were found.The predominance of meta- and para-substituted products is attributed to steric effects.The evidence that the reaction proceeds via a purine radical includes light stimulation, relative insensitivity to electronic factors, and the facile reaction of the purine intermediate with pyridine N-oxide.Photolysis of 6-iodo-9-benzylpurine in the presence of anisole gave the same mixture of 6-(m-methoxyphenyl)- and 6-(p-methoxyphenyl)purine as did diazotization, suggesting that both reactions involve the same purine radical.