Formation of an Unexpected 2-Deoxy-α-D-Threo-Pentofuranosyl Azide by Reaction of O²,3′-Anhydro-5′-O-trityl-2′-deoxycytidine with Lithium Azide

I. A. Mikhailopulo Institute of Bioorganic Chemistry, Byelorussian Academy of Sciences, 220600, Minsk, USSR

G. V. Zaitseva Institute of Bioorganic Chemistry, Byelorussian Academy of Sciences, 220600, Minsk, USSR

E. V. Vaaks Institute of Bioorganic Chemistry, Byelorussian Academy of Sciences, 220600, Minsk, USSR

H. Rosemeyer Laboratorium für Organische und Bioorganische Chemie, Fachbereich Biologie/Chemie, Universität Osnabrück, D-4500, Osnabrück, Germany

F. Seela Laboratorium für Organische und Bioorganische Chemie, Fachbereich Biologie/Chemie, Universität Osnabrück, D-4500, Osnabrück, Germany

Abstract

Reaction of 0²,3′-anhydro-5′-0-trityl-2′-deoxycytidine (1) with LiN₃s in DMF resulted in the formation of 1-(3-azido-2,3-dideoxy-5-0-trityl-β-D-erythro-pentofuranosyl) cytosine (2) and 3-0-(4-amino-1,3-pyrimidin-2-yl)-5-0-trityl-2-deoxy-α-D-threo-pentofuranosyl azide (3) (2:3 = 1:1) in 88% yield. Compound 3 was deprotected with 80% aqueous AcOH yielding 4

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Formation of an Unexpected 2-Deoxy-α-D-Threo-Pentofuranosyl Azide by Reaction of O²,3′-Anhydro-5′-O-trityl-2′-deoxycytidine with Lithium Azide

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Formation of an Unexpected 2-Deoxy-α-D-Threo-Pentofuranosyl Azide by Reaction of O2,3′-Anhydro-5′-O-trityl-2′-deoxycytidine with Lithium Azide

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Formation of an Unexpected 2-Deoxy-α-D-Threo-Pentofuranosyl Azide by Reaction of O²,3′-Anhydro-5′-O-trityl-2′-deoxycytidine with Lithium Azide