4803-92-3Relevant academic research and scientific papers
Chemoenzymatic synthesis of 3′-O-acetal-protected 2′-deoxynucleosides as building blocks for nucleic acid chemistry
Rodriguez-Perez, Tatiana,Fernandez, Susana,Martinez-Montero, Saul,Gonzalez-Garcia, Tania,Sanghvi, Yogesh S.,Gotor, Vicente,Ferrero, Miguel
experimental part, p. 1736 - 1744 (2010/06/13)
We have developed a simple and convenient synthetic strategy for the preparation of tetrahydropyranyl, 4-methoxy-tetrahydropyranyl, and tetrahydrofuranyl ethers of 2′-deoxynucleosides, which are useful building blocks for nucleic acid chemistry. Enzymatic benzoylation provides an efficient alternative for protecting the 5′-hydroxy group of the parent nucleosides in a regioselective manner. Subsequently, tetrahydropyranylation and tetrahydrofuranylation of the 2′-deoxynucleosides at the 3′-hydroxy group were accomplished with p-toluensulfonic acid, MgBr2, or camphorsulfonic acid as catalysts. Deprotection of the 5′-O-benzoyl group furnished 3′-O-acetal-protected 2′-deoxynucleosides. The three-step process is expected to enable the large-scale synthesis of protected nucleosides.
A mild, efficient and regioselective enzymatic procedure for 5′-O-benzoylation of 2′-deoxynucleosides
García, Javier,Fernández, Susana,Ferrero, Miguel,Sanghvi, Yogesh S.,Gotor, Vicente
, p. 1709 - 1712 (2007/10/03)
Lipase from Candida antarctica B catalyzes the selective monobenzoylation at the 5′-hydroxyl group of 2′-deoxynucleosides using vinyl benzoate as acyl transfer reagent in quantitative yields. The industrial suitability of this process via the reclaim and reuse of enzyme and vinyl benzoate has been demonstrated.
