Electrophilic Substitution at C(7) of a Protected 7-Deaza-2’-deoxyguanosine – The 2’-Deoxyribonucleoside Parent Analogue of Queuosine #

doi:10.3390/M522

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Molbank 2007, 2007(1), M522; doi:10.3390/M522

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Electrophilic Substitution at C(7) of a Protected 7-Deaza-2’-deoxyguanosine – The 2’-Deoxyribonucleoside Parent Analogue of Queuosine^#

Natalya Ramzaeva and Helmut Rosemeyer*

Organische Chemie I – Bioorganische Chemie, Institut für Chemie, Fachbereich Biologie/Chemie, Universität Osnabrück, Barbarastr. 7, D-49069 Osnabrück, Germany

* Author to whom correspondence should be addressed.

Received: 28 March 2007 / Accepted: 4 April 2007 / Published: 23 April 2007

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Abstract: In this manuscript we report on the regioselective electrophilic substitution at C(7) of 7-[2-deoxy-3,5-bis-O-(2-methylpropanoyl)-ß-D-erythro-pentofuranosyl]-2-(formylamino)-4-methoxy-7H-pyrrolo[2,3-d]pyrimidine (2) – a protected precursor of 7-deaza-2’-deoxyguanosine - using N,N-dimethyl-methyleniminium iodide (Eschenmoser’s salt) yielding the Mannich compound 4.

Keywords: 7-Deazapurine; Mannich bases; Eschenmoser’s Salt

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MDPI and ACS Style

Ramzaeva, N.; Rosemeyer, H. Electrophilic Substitution at C(7) of a Protected 7-Deaza-2’-deoxyguanosine – The 2’-Deoxyribonucleoside Parent Analogue of Queuosine^#. Molbank 2007, 2007, M522.

AMA Style

Ramzaeva N., Rosemeyer H. Electrophilic Substitution at C(7) of a Protected 7-Deaza-2’-deoxyguanosine – The 2’-Deoxyribonucleoside Parent Analogue of Queuosine^#. Molbank. 2007; 2007(1):M522.

Chicago/Turabian Style

Ramzaeva, Natalya; Rosemeyer, Helmut. 2007. "Electrophilic Substitution at C(7) of a Protected 7-Deaza-2’-deoxyguanosine – The 2’-Deoxyribonucleoside Parent Analogue of Queuosine^#." Molbank 2007, no. 1: M522.

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