Nucleotide. XV. Synthese und Eigenschaften von 2′-O-t-Butyldimethylsilyl-5′-O-monomethoxytritylribonucleosid-3′-phosphotriestern, Ausgangssubstanzen für Oligonucleotid-Synthesen
✍ Scribed by Gunter Silber; Dieter Flockerzi; Rajendra Singh Varma; Ramamurthy Charubala; Eugen Uhlmann; Wolfgang Pfleiderer
- Publisher
- John Wiley and Sons
- Year
- 1981
- Tongue
- German
- Weight
- 753 KB
- Volume
- 64
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Nucleotides. XV. Synthesis and Properties of 2′O‐t‐Butyldimethylsilyl‐5′‐O‐monomethoxytritylribonucleoside‐3′‐phosphotriesters, Starting Materials for Oligonucleotide Syntheses
The syntheses of two types of fully blocked ribonucleoside 3′‐phosphotriesters 6–14 have been achieved in excellent yields from 2′‐O‐t‐butyldimethylsilyl‐5′‐O‐monomethoxytrityl‐ribonucleosides 1–5 by phosphorylation with 2‐chloro‐ and 2,5‐dichlorophenylphosphorodichloridate respectively and subsequent treatment by cyanoethanol to 6, 8, 10, 12 and 14 and by p‐nitrophenylethanol to 7, 9, 11 and 13. These phosphotriesters are valuable starting materials for oligonucleotide syntheses due to the fact that the corresponding phosphotriesters 15–23 with free HOC(5′) could be obtained by detritylation and the 3′‐phosphodiester triethylammonium salts 24–32 by deblocking of the cyanoethyl and the 2,5‐dichlorophenyl group respectively. All newly synthesized compounds have been characterized by UV.‐and NMR.‐spectra as well as C, H, N elementary analyses.