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Nucleotide. XV . Synthese und Eigenschaften von 2′‐ O ‐ t ‐Butyldimethylsilyl‐5′‐ O ‐monomethoxytritylribonucleosid‐3′‐phosphotriestern, Ausgangssubstanzen für Oligonucleotid‐Synthesen
Author(s) -
Silber Gunter,
Flockerzi Dieter,
Varma Rajendra Singh,
Charubala Ramamurthy,
Uhlmann Eugen,
Pfleiderer Wolfgang
Publication year - 1981
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19810640548
Subject(s) - chemistry , phosphodiester bond , oligonucleotide , ribonucleoside , stereochemistry , nucleotide , oligonucleotide synthesis , nuclear magnetic resonance spectroscopy , dna , biochemistry , rna , gene
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.