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
Synthesis of 5-(β-D-glucopyranosyloxymethyl)-2′-deoxyuridine and derivatives thereof. A modified d-nucleoside from the DNA of Trypanosoma brucei
✍ Scribed by E. R. Wijsman; O. van den Berg; E. Kuyl-Yeheskiely; G. A. van der Marel; J. H. van Boom
- Publisher
- Elsevier Science
- Year
- 2010
- Tongue
- English
- Weight
- 198 KB
- Volume
- 113
- Category
- Article
- ISSN
- 0165-0513
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✦ Synopsis
Abstract
An appropriately protected 3′‐phosphoramidite and 5′‐phosphate derivative of the modified 2′‐deoxyuridine were obtained by β‐glycosylation of a properly protected 5‐hydroxymethyl‐2′‐deoxyuridine, and subsequent elaboration of the resulting intermediates using standard protocols devised in nucleic acids chemistry.
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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
## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v