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Reinvestigation into the Synthesis of Oligonucleotides Containing 5-(β-D-Glucopyranosyloxymethyl)-2′-deoxyuridine.

✍ Scribed by John J. Turner; Nico J. Meeuwenoord; Anita Rood; Piet Borst; Gijs A. van der Marel; Jacques H. van Boom

Publisher
John Wiley and Sons
Year
2004
Weight
54 KB
Volume
35
Category
Article
ISSN
0931-7597

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Reinvestigation into the Synthesis of Ol
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## Abstract A reinvestigation into the synthesis of oligonucleotides containing 5‐(β‐D‐glucopyranosyloxymethyl)‐2′‐deoxyuridine revealed that existing procedures for the preparation of these DNA fragments suffered from decomposition at the final deprotection step. The decomposition product was iden

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The synthesis of the recently discovered modified DNA base derivative 20, readily available from thymidine in 48%, afforded the fully protected nucleoside 22 in 96% yield. The 5-(β-D-glucopyranosyloxymethyl)-2Ј-deoxyuridine (β-dJ, 1) is described. TMSOTf mediated β-glucosylation of latter compound w