Nucleotides, Part 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 building blocks for oligonu...
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Published in | Helvetica chimica acta Vol. 82; no. 12; pp. 2172 - 2185 |
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Main Authors | , , , , , , , |
Format | Journal Article |
Language | English |
Published |
Basel
Verlag Helvetica Chimica Acta
15.12.1999
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Online Access | Get full text |
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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 O6‐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]‐O6‐[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 O4‐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). |
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Bibliography: | istex:CAD7011D31BBF4EB1F5F9CF7AE82BB840ECC24B9 ArticleID:HLCA2172 ark:/67375/WNG-2N8Q7C8Q-F ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0018-019X 1522-2675 |
DOI: | 10.1002/(SICI)1522-2675(19991215)82:12<2172::AID-HLCA2172>3.0.CO;2-R |