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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Autores principales:	Caballero, G., Gallo, M., Montserrat, J.M., Iribarren, A.M.
Formato:	JOUR
Materias:	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
Acceso en línea:	http://hdl.handle.net/20.500.12110/paper_0018019X_v85_n5_p1284_Caballero
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	todo:paper_0018019X_v85_n5_p1284_Caballero
record_format	dspace
spelling	todo:paper_0018019X_v85_n5_p1284_Caballero2023-10-03T14:15:08Z Synthesis of (2′s)-2′-deoxy-2′-C-methylpurine nucleosides and their phosphoramidites Caballero, G. Gallo, M. Montserrat, J.M. Iribarren, A.M. 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). JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar 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 Caballero, G. Gallo, M. Montserrat, J.M. Iribarren, A.M. 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).
format	JOUR
author	Caballero, G. Gallo, M. Montserrat, J.M. Iribarren, A.M.
author_facet	Caballero, G. Gallo, M. Montserrat, J.M. Iribarren, A.M.
author_sort	Caballero, G.
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
url	http://hdl.handle.net/20.500.12110/paper_0018019X_v85_n5_p1284_Caballero
work_keys_str_mv	AT caballerog synthesisof2s2deoxy2cmethylpurinenucleosidesandtheirphosphoramidites AT gallom synthesisof2s2deoxy2cmethylpurinenucleosidesandtheirphosphoramidites AT montserratjm synthesisof2s2deoxy2cmethylpurinenucleosidesandtheirphosphoramidites AT iribarrenam synthesisof2s2deoxy2cmethylpurinenucleosidesandtheirphosphoramidites
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Synthesis of (2′s)-2′-deoxy-2′-C-methylpurine nucleosides and their phosphoramidites

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