Synthesis of Chlorodideoxynucleosides Using Tris(2,4,6-tribromophenoxy)-dichlorophosphorane (BDCP) |
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| Authors: | R K Singh S Ohuchi T Wada T Hata# |
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| Institution: | 1. Nucleic Acids Research Laboratory, Department of Chemistry , University of Allahabad , Allahabad, 211002, India;2. Department of Life Chemistry , Tokyo Institute of Technology , Nagatsuta, Midoriku, Yokohama, 227 |
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| Abstract: | Abstract 5′-Chloro-5′-deoxy-N,3′-O-dibenzoylthymidine (3a), 5′-chloro-5′-deoxy-N4, 3′-O-dibenzoyldeoxycytidine(3b), 5′-chloro-5′-deoxy-N6,3′-O-dibenzoyldeoxyadenosine(3c), N-benzoyl-1-(3-chloro-2,3-dideoxy-5-O-trityl-ß-D-xylofuranosyl)thymine (5a) and N6-benzoyl-9-(3-chloro-2,3-dideoxy-5-O-trityl-ß-D-xylofuranosyl)adenine (5b) have been synthesized in very high yields using a new efficient reagent, tris(2,4,6-tribrom-ophenoxy)dichlorophosphorane (BDCP). The reaction time was greatly reduced to 5–8 min. NOE data suggested an inversion of configuration at C3-position and thus an SN2 mechanism has been proposed for the chlorination reaction. |
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