Functionalization of Guanosine and 2′‐Deoxyguanosine at C6: A Modified Appel Process and S_NAr Displacement of Imidazole

Abstract

Treatment of sugar‐protected 2‐N‐trityl derivatives of guanosine and 2′‐deoxyguanosine with imidazole/triphenylphosphine/iodine/ethyldiisopropylamine gives the corresponding 6‐(imidazol‐1‐yl)‐2‐(tritylamino)purine nucleosides. S_NAr displacement of the imidazole moiety with nucleophiles provides 2‐amino‐6‐substituted‐purine nucleosides and 2′‐deoxynucleosides.

^†In honor and celebration of the 70th birthday of Professor Leroy B. Townsend.

^#This paper is: Nucleic Acid Related Compounds, 122. Paper 121 is Ref. 1.

Keywords:

• 2‐Amino‐6‐substituted‐purine nucleosides and 2′‐deoxynucleosides
• 2′‐Deoxyguanosine derivatives
• Guanosine derivatives
• Guanine nucleoside modifications

Acknowledgments

We are grateful for Graduate Research Fellowships from Brigham Young University (X.L.) and pharmaceutical company gift funds (M.J.R.) for financial support.

Notes

^†In honor and celebration of the 70th birthday of Professor Leroy B. Townsend.

^#This paper is: Nucleic Acid Related Compounds, 122. Paper 121 is Ref. 1.