A1 Journal article – refereed

Preparation of a disulfide-linked precipitative soluble support for solution-phase synthesis of trimeric oligodeoxyribonucleotide 3´-(2-chlorophenylphosphate) building blocks




List of Authors: Amit M. Jabgunde, Alejandro Gimenez Molina, Pasi Virta, Harri Lönnberg

Publication year: 2015

Journal: Beilstein Journal of Organic Chemistry

Volume number: 11

Number of pages: 8

ISSN: 1860-5397

DOI: http://dx.doi.org/10.3762/bjoc.11.171

URL: http://www.beilstein-journals.org/bjoc/single/articleFullText.htm?publicId=1860-5397-11-171


Abstract

The preparation of a disulfide-tethered precipitative soluble support and its use for solution-phase synthesis of trimeric oligodeoxyribonucleotide 3'-(2-chlorophenylphosphate) building blocks is described. To obtain the building blocks, N-acyl protected 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)ribonucleosides were phosphorylated with bis(benzotriazol-1-yl) 2-chlorophenyl phosphate. The "outdated" phosphotriester strategy, based on coupling of P-V building blocks in conjunction with quantitative precipitation of the oligodeoxyribonucleotide with MeOH is applied. Subsequent release of the resulting phosphate and base-protected oligodeoxyribonucleotide trimer 3'-pTpdCBzpdGibu-5' as its 3'-(2-chlorophenyl phosphate) was achieved by reductive cleavage of the disulfide bond.


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