Synthesis of (2′s)-2′-deoxy-2′-C-methylpurine nucleosides and their phosphoramidites
We describe the stereoselective synthesis of (2′S)-2′-deoxy-2′-C-methyladenosine (12) and (2′S)-2′-deoxy-2′-C-methylinosine (14) as well as their corresponding cyanoethyl phosphoramidites 16 and 19 from 6-0-(2,6-dichlorophenyl)inosine as starting material. The methyl group at the 2′-position was int...
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2002
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Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0018019X_v85_n5_p1284_Caballero http://hdl.handle.net/20.500.12110/paper_0018019X_v85_n5_p1284_Caballero |
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paper:paper_0018019X_v85_n5_p1284_Caballero2023-06-08T14:39:09Z Synthesis of (2′s)-2′-deoxy-2′-C-methylpurine nucleosides and their phosphoramidites Alcohols Oxidation Reduction Stereochemistry Moieties Synthesis (chemical) 2' deoxy 2' c methyladenosine 2' deoxy 2' c methylinosine 2' deoxy 2' c methylpurine nucleoside nucleoside derivative phosphoramidic acid derivative unclassified drug article catalysis chemical analysis drug synthesis oxidation priority journal stereochemistry We describe the stereoselective synthesis of (2′S)-2′-deoxy-2′-C-methyladenosine (12) and (2′S)-2′-deoxy-2′-C-methylinosine (14) as well as their corresponding cyanoethyl phosphoramidites 16 and 19 from 6-0-(2,6-dichlorophenyl)inosine as starting material. The methyl group at the 2′-position was introduced via a Wittig reaction (→ 3, Scheme 1) followed by a stereoselective oxidation with OsO4 (→ 4, Scheme 2). The primary-alcohol moiety of 4 was tosylated (→5) and regioselectively reduced with NaBH4 (→6). Subsequent reduction of the 2′-alcohol moiety with Bu3SnH yielded stereoselectively the corresponding (2′S)-2′-deoxy-2′-C-methylnucleoside (→8a). 2002 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0018019X_v85_n5_p1284_Caballero http://hdl.handle.net/20.500.12110/paper_0018019X_v85_n5_p1284_Caballero |
institution |
Universidad de Buenos Aires |
institution_str |
I-28 |
repository_str |
R-134 |
collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
topic |
Alcohols Oxidation Reduction Stereochemistry Moieties Synthesis (chemical) 2' deoxy 2' c methyladenosine 2' deoxy 2' c methylinosine 2' deoxy 2' c methylpurine nucleoside nucleoside derivative phosphoramidic acid derivative unclassified drug article catalysis chemical analysis drug synthesis oxidation priority journal stereochemistry |
spellingShingle |
Alcohols Oxidation Reduction Stereochemistry Moieties Synthesis (chemical) 2' deoxy 2' c methyladenosine 2' deoxy 2' c methylinosine 2' deoxy 2' c methylpurine nucleoside nucleoside derivative phosphoramidic acid derivative unclassified drug article catalysis chemical analysis drug synthesis oxidation priority journal stereochemistry Synthesis of (2′s)-2′-deoxy-2′-C-methylpurine nucleosides and their phosphoramidites |
topic_facet |
Alcohols Oxidation Reduction Stereochemistry Moieties Synthesis (chemical) 2' deoxy 2' c methyladenosine 2' deoxy 2' c methylinosine 2' deoxy 2' c methylpurine nucleoside nucleoside derivative phosphoramidic acid derivative unclassified drug article catalysis chemical analysis drug synthesis oxidation priority journal stereochemistry |
description |
We describe the stereoselective synthesis of (2′S)-2′-deoxy-2′-C-methyladenosine (12) and (2′S)-2′-deoxy-2′-C-methylinosine (14) as well as their corresponding cyanoethyl phosphoramidites 16 and 19 from 6-0-(2,6-dichlorophenyl)inosine as starting material. The methyl group at the 2′-position was introduced via a Wittig reaction (→ 3, Scheme 1) followed by a stereoselective oxidation with OsO4 (→ 4, Scheme 2). The primary-alcohol moiety of 4 was tosylated (→5) and regioselectively reduced with NaBH4 (→6). Subsequent reduction of the 2′-alcohol moiety with Bu3SnH yielded stereoselectively the corresponding (2′S)-2′-deoxy-2′-C-methylnucleoside (→8a). |
title |
Synthesis of (2′s)-2′-deoxy-2′-C-methylpurine nucleosides and their phosphoramidites |
title_short |
Synthesis of (2′s)-2′-deoxy-2′-C-methylpurine nucleosides and their phosphoramidites |
title_full |
Synthesis of (2′s)-2′-deoxy-2′-C-methylpurine nucleosides and their phosphoramidites |
title_fullStr |
Synthesis of (2′s)-2′-deoxy-2′-C-methylpurine nucleosides and their phosphoramidites |
title_full_unstemmed |
Synthesis of (2′s)-2′-deoxy-2′-C-methylpurine nucleosides and their phosphoramidites |
title_sort |
synthesis of (2′s)-2′-deoxy-2′-c-methylpurine nucleosides and their phosphoramidites |
publishDate |
2002 |
url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0018019X_v85_n5_p1284_Caballero http://hdl.handle.net/20.500.12110/paper_0018019X_v85_n5_p1284_Caballero |
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1768541923069394944 |