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Paper | Regular issue | Vol 48, No. 11, 1998, pp.2339-2345
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8313
■ A Novel Synthesis of C-Nucleosides Having Pyrrolo[1,2-f]pteridine, 6- and 8-Deazapyrrolo[1,2-f]pteridine Ring Systems from 6-Hydroxy-6-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2H-pyran-3(6H)-one

Natsu Nishimura, Yoshitada Hasegawa, Souhei Mizuno, Misa Yuasa, and Isamu Maeba*

*Faculty of Pharmacy, Meijo University, 150 Yagotoyama, Tenpaku, Nagoya 468-8503, Japan

Abstract

A versatile intermediate pyranulose glycoside (1) for C-nucleoside synthesis was treated with 4,5-diaminopyrimidine in AcOH to give 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyrrolo[1,2-f]pteridine (2) in 58% yield. However, treatement of 1 with 4,5,6-triaminopyrimidine in TFA afforded the 4-aminopteridine (4) without formation of the pyrrolo[1,2-f]pteridine. Similar reaction of 2,3- and 3,4-diaminopyridines with 1 in AcOH led to formation of 8- and 6-deazapyrrolo[1,2-f]pteridines (5 and 6), respectively. Removal of the sugar protecting groups in 2, 5, and 6 with sodium carbonate gave the deprotected C-nucleosides (7, 8 and 9).