An efficient process for synthesis of 2'-O-methyl and 3'-O-methyl guanosine from 2-aminoadenosine using diazomethane and the catalyst stannous chloride

Nucleosides, Nucleotides & Nucleic Acids
Anilkumar R KoreSrinu Reddy

Abstract

An improved strategy for the selective synthesis of 2'-O-methyl and 3'-O-methyl guanosine from 2-aminoadenosine is reported by using the catalyst stannous chloride. The regioselectivity of the 2' and 3'-O-alkylation was achieved by optimizing the addition, timing, and concentration of the catalysts and diazomethane during the methylation reaction. An efficient and selective alkylation at 2'-OH of 2-aminoadenosine was achieved by mixing a stoichiometric amount of stannous chloride at room temperature in DME The reaction mixture was stirred at 50 degrees C for 1 min and immediately followed by addition of diazomethane. The resulting 2'-O-methyl 2-aminoadenosine was treated with the enzyme adenosine deaminase, which resulted in an efficient conversion to the desired 2'-O-methylguanosine (98% yield). The product was isolated by crystallization. In contrast, the methylation at 3'-OH of 2-aminoadenosine was achieved by mixing a stoichiometric amount of stannous chloride in DMF and stirring at 50 degrees C for 15 min, followed by addition of diazomethane. The resulting mixture containing 3'-O-methyl-2-aminoadenosine in 90% yield and 2'-O-methyl-2-aminoadenosine in 10% yield was treated with the enzyme adenosine deaminase, which prefer...Continue Reading

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Citations

Dec 1, 2009·Bioorganic & Medicinal Chemistry Letters·Tsuyoshi MukobataHidehito Urata
Jan 8, 2008·Bioorganic & Medicinal Chemistry Letters·Anilkumar R Kore, Muthian Shanmugasundaram
Sep 10, 2013·Chemistry : a European Journal·Yong WangMichio Kurosu

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Methods Mentioned

BETA
ion-exchange chromatography
deamination

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