Artículo
Caballero, G.; Gallo, M.; Montserrat, J.M.; Iribarren, A.M. "Synthesis of (2′s)-2′-deoxy-2′-C-methylpurine nucleosides and their phosphoramidites" (2002) Helvetica Chimica Acta. 85(5):1284-1294
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Abstract:
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).
Registro:
| Documento: | Artículo |
| Título: | Synthesis of (2′s)-2′-deoxy-2′-C-methylpurine nucleosides and their phosphoramidites |
| Autor: | Caballero, G.; Gallo, M.; Montserrat, J.M.; Iribarren, A.M. |
| Filiación: | Instituto di Ricerche di Biologia Molecolare (RBM), Roma, Italy Inst. de Invest. en Ingeniería Genética y Biología Molecular (INGEBI), CONICET, Vuelta de Obligado 24902oP, (1428) Buenos Aires, Argentina Universidad Nacional de Quilmes, Bernal, Argentina |
| Palabras clave: | 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 |
| Año: | 2002 |
| Volumen: | 85 |
| Número: | 5 |
| Página de inicio: | 1284 |
| Página de fin: | 1294 |
| DOI: | http://dx.doi.org/10.1002/1522-2675(200205)85:5<1284::AID-HLCA1284>3.0.CO;2-S |
| Título revista: | Helvetica Chimica Acta |
| Título revista abreviado: | Helv. Chim. Acta |
| ISSN: | 0018019X |
| CODEN: | HCACA |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0018019X_v85_n5_p1284_Caballero |
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Citas:
---------- APA ----------
Caballero, G., Gallo, M., Montserrat, J.M. & Iribarren, A.M. (2002) . Synthesis of (2′s)-2′-deoxy-2′-C-methylpurine nucleosides and their phosphoramidites. Helvetica Chimica Acta, 85(5), 1284-1294.http://dx.doi.org/10.1002/1522-2675(200205)85:5<1284::AID-HLCA1284>3.0.CO;2-S
---------- CHICAGO ----------
Caballero, G., Gallo, M., Montserrat, J.M., Iribarren, A.M. "Synthesis of (2′s)-2′-deoxy-2′-C-methylpurine nucleosides and their phosphoramidites" . Helvetica Chimica Acta 85, no. 5 (2002) : 1284-1294.http://dx.doi.org/10.1002/1522-2675(200205)85:5<1284::AID-HLCA1284>3.0.CO;2-S
---------- MLA ----------
Caballero, G., Gallo, M., Montserrat, J.M., Iribarren, A.M. "Synthesis of (2′s)-2′-deoxy-2′-C-methylpurine nucleosides and their phosphoramidites" . Helvetica Chimica Acta, vol. 85, no. 5, 2002, pp. 1284-1294.http://dx.doi.org/10.1002/1522-2675(200205)85:5<1284::AID-HLCA1284>3.0.CO;2-S
---------- VANCOUVER ----------
Caballero, G., Gallo, M., Montserrat, J.M., Iribarren, A.M. Synthesis of (2′s)-2′-deoxy-2′-C-methylpurine nucleosides and their phosphoramidites. Helv. Chim. Acta. 2002;85(5):1284-1294.http://dx.doi.org/10.1002/1522-2675(200205)85:5<1284::AID-HLCA1284>3.0.CO;2-S
