Synthesis of 8‐Substituted 2′‐Deoxyisoguanosines via Unprotected 8‐Brominated 2‐Amino‐2′‐deoxyadenosine. Issue 1 (27th December 2017)

• Record Type: Journal Article
• Authors: Zhang, Wen; Gao, Qian; Wei, Shuxian; Fu, Bicheng; Yang, Qian; Ming, Xin
• Is Part Of: Chemistry & biodiversity. Volume 15:Issue 1(2018)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2017-12-27
• Subjects: 8‐alkynylated purine nucleosides -- bromination -- cross‐coupling reaction -- microwave assistance; Biochemistry -- Periodicals; Molecular biology -- Periodicals; Biodiversity -- Periodicals; 572
• DOI: 10.1002/cbdv.201700335
• Languages: English
• ISSNs: 1612-1872

Abstract

Abstract : A variety of applications of 8‐alkynylated nucleosides has prompted the synthesis of new purine analogues. Bromination of unprotected 2‐amino‐2′‐deoxyadenosine with Br2 /AcOH/AcONa gives 2‐amino‐8‐bromo‐2′‐deoxyadenosine (87%). The brominated derivative is converted to 8‐alkynylated 2‐amino‐2′‐deoxyadenosines by palladium‐catalyzed Sonogashira cross‐coupling reaction via microwave assistance (81 – 95%). The resulting compounds are further transformed to 8‐alkynylated 2′‐deoxyisoguanosines (52 – 70%). The physical properties of new compounds are investigated. Abstract :