Study on Disulfur-Backboned Nucleic Acid: Part 1, Efficient Synthesis of 3′,5′-Dithio-2′-Deoxyadenosine

Abstract An efficient procedure is established to synthesize 3′,5′-dithio-2′-deoxyadenosine starting from 2′-deoxyadenosine in five steps in 33% overall yield. In this procedure, the key intermediate 9 was synthesized by twice S N 2 reactions with twice 3′-configuration inversions and then it was de...

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Bibliographic Details
Published in:Synlett 2004-11, Vol.2004 (14), p.2585-2587
Main Authors: Zheng, Hongchao, Cheng, Changmei, Wang, Hua, Xu, Shanshan, Zhao, Yufen
Format: Article
Language:English
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Summary:Abstract An efficient procedure is established to synthesize 3′,5′-dithio-2′-deoxyadenosine starting from 2′-deoxyadenosine in five steps in 33% overall yield. In this procedure, the key intermediate 9 was synthesized by twice S N 2 reactions with twice 3′-configuration inversions and then it was deprotected to title compound by removing three acyl groups in one pot.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2004-834809