Facile Synthesis of 2′‐Deoxyisoguanosine and Related 2′,3′‐Dideoxyribonucleosides

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Abstract
The 2′‐deoxyisoguanosine (1) was synthesized by a two‐step procedure from 2′‐deoxyguanosine (5). Amination of silylated 2′‐deoxyguanosine yielded 2‐amino‐2′‐deoxyadenosine (6) which was subjected to selective deamination of the 2‐NH2 group resulting in compound 1. Also 2′,3′‐dideoxyisoguanosine (2) was prepared employing the photo‐substitution of the 2‐substituent of 2‐chloro‐2′,3′‐dideoxyadenosine (4). The latter was synthesized by Barton deoxygenation from 2‐chloro‐2′‐deoxyadenosine (3) or via glycosylation of 2,6‐dichloropurine (12) with the lactol 13. Compound 1 was less stable at the N‐glycosylic bond than 2′‐deoxyguanosine (5). The dideoxynucleoside 2 was deaminated by adenosine deaminase affording 2′,3′‐dideoxyxanthosine (17).