Improved and Reliable Synthesis of 3′-Azido-2′,3′-dideoxyguanosine Derivatives

An improved synthesis of N 2 -protected-3′-azido-2′,3′-dideoxyguanosine 20 and 23 is described. Deoxygenation of 2′-O-alkyl (and/or aryl) sulfonyl-5′-dimethoxytritylguanosine coupled with [1,2]-hydride shift rearrangement gave protected 9-(2-deoxy-threo-pentofuranosyl)guanines ( 10 , 12 and 16 ). Th...

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Bibliographic Details
Published in:Nucleosides, nucleotides & nucleic acids nucleotides & nucleic acids, 2004-01, Vol.23 (1-2), p.171-181
Main Authors: Timoshchuk, Victor A., Hogrefe, Richard I., Vaghefi, Morteza M.
Format: Article
Language:English
Subjects:
3′-Azido-2
3′-dideoxyguanosine
Anti-HIV Agents - chemical synthesis
Anti-HIV Agents - chemistry
Dideoxynucleosides - chemical synthesis
Dideoxynucleosides - chemistry
l-Selectride
Magnetic Resonance Spectroscopy
Mass Spectrometry
Rearrangement
Reduction
Stereoselectivity
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Summary:An improved synthesis of N 2 -protected-3′-azido-2′,3′-dideoxyguanosine 20 and 23 is described. Deoxygenation of 2′-O-alkyl (and/or aryl) sulfonyl-5′-dimethoxytritylguanosine coupled with [1,2]-hydride shift rearrangement gave protected 9-(2-deoxy-threo-pentofuranosyl)guanines ( 10 , 12 and 16 ). This rearrangement was accomplished in high yield with a high degree of stereoselectivity using lithium triisobutylborohydride (l-Selectride®). Compounds 10 , 12 and 16 were transformed into 3′-O-mesylates ( 18 and 21 ), which can be used for 3′-substitution. The 3′-azido nucleosides were obtained by treatment of 18 and 21 with lithium azide. This procedure is reproducible with a good overall yield. † In honor and celebration of the 70th birthday of Professor Leroy B. Townsend.
ISSN:1525-7770
1532-2335
DOI:10.1081/NCN-120027826