Nucleotides - LXIII - New 2-(4-nitrophenyl)ethyl(npe)- and 2-(4-nitrophenyl)ethoxycarbonyl(npeoc)-protected 2 '-deoxyribonucleosides and their 3 '-phosphoramidites - Versatile building blocks for oligonucleotide synthesis

A series of new base-protected and 5'-O-(4-monomethoxytrityl)- or 5'-O-(4,4'-dimethoxytrityl)-substituted 3'-(2-cyanoethyl diisopropylphosphoramidites) and 3'-[2-(4-nitrophenyl)ethyl diisopropylphosphoramidites] 52-66 and 67-82, respectively, are prepared as potential buildi...

Full description

Saved in:
Bibliographic Details
Published inHelvetica chimica acta Vol. 82; no. 12; pp. 2172 - 2185
Main Authors Lang, H, Gottlieb, M, Schwarz, M, Farkas, S, Schulz, BS, Himmelsbach, F, Charubala, R, Pfleiderer, W
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.01.1999
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
OLIGODEOXYNUCLEOTIDES
PROTECTION
SOLID-PHASE SYNTHESIS
NUCLEOSIDES
PHOSPHORAMIDITE APPROACH
OLIGODEOXYRIBONUCLEOTIDES
DERIVATIVES
RESIDUES
CHEMICAL SYNTHESIS
SIDE REACTIONS
Online AccessGet full text

Cover

More Information
Summary:A series of new base-protected and 5'-O-(4-monomethoxytrityl)- or 5'-O-(4,4'-dimethoxytrityl)-substituted 3'-(2-cyanoethyl diisopropylphosphoramidites) and 3'-[2-(4-nitrophenyl)ethyl diisopropylphosphoramidites] 52-66 and 67-82, respectively, are prepared as potential building blocks for oligonucleotide synthesis (see Scheme). Thus, 3',5'-di-O-acyl- and N-2,3'-O,5'-O-triacyl-2'-deoxyguanosines can easily be converted into the corresponding O-6-alkyl derivatives 6, 8, 10, 12, 14, and 16 by a Mitsunobu reaction using the appropriate alcohol. Mild hydrolysis removes the acyl groups from the sugar moiety (--> 9, 11, 13, 15, and 19 (via 18), resp.) which can then be tritylated (--> 38-42) and phosphitylated (--> 57-61) in the usual manner. N-2-[2-(4-nitrophenyl)ethoxycarbonyl]-substituted and N-2-[2-(4-nitrophenyl)ethoxycarbonyl]-O-6-[2-(4-nitrophenyl)ethyl]-substituted 2'-deoxyguanosines 5 and 7, respectively, are synthesized as new starting materials for tritylation (--> 28, 35, and 37) and phosphitylation (--> 54, 56, 70, and 78). Various O-4-alkylthymidines (see 20-24) are also converted to their 5'-O-dimethoxytrityl derivatives (see 43-47) and the corresponding phosphoramidites (see 62-66 and 79-82).
ISSN:0018-019X
DOI:10.1002/(SICI)1522-2675(19991215)82:12<2172::AID-HLCA2172>3.0.CO;2-R