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Title: Diversely C8-functionalized adenine nucleosides via their underexplored carboxaldehydes
The potentially versatile N-unprotected 8-formyl derivatives of adenosine and 2’-deoxyadenosine are highly underexploited for C8 modifications of these nucleosides. Only in situ formation of 8-formyladenosine is known and a single application of an N-benzoyl derivative has been reported. On the other hand, 8-formyl-2’-deoxyadenosine and its applications remain unknown. Herein, we report straightforward, scalable syntheses of both N-unprotected 8-formyladenine nucleoside derivatives, and demonstrate broad diversification at the C8 position by hydroxymethylation, azidation, CuAAC ligation, reductive amination, as well as olefination and fluoroolefination with modified Julia and a Horner-Wadsworth-Emmons reagents.  more » « less
Award ID(s):
1953574
PAR ID:
10315900
Author(s) / Creator(s):
; ; ; ; ;
Publisher / Repository:
Royal Society of Chemistry
Date Published:
Journal Name:
Chemical Communications
Volume:
58
Issue:
11
ISSN:
1359-7345
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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