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- Title
Nucleotide. XV. Synthese und Eigenschaften von 2′- O- t-Butyldimethylsilyl-5′- O-monomethoxytritylribonucleosid-3′-phosphotriestern, Ausgangssubstanzen für Oligonucleotid-Synthesen.
- Authors
Silber, Gunter; Flockerzi, Dieter; Varma, Rajendra Singh; Charubala, Ramamurthy; Uhlmann, Eugen; Pfleiderer, Wolfgang
- Abstract
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.
- Publication
Helvetica Chimica Acta, 1981, Vol 64, Issue 5, p1704
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19810640548