Synthesis of C-Nucleoside Analogues Starting from 1-(Methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-a-D-altropyranosid-2-yl)-4-ph enyl-but- 3-yn-2-one 1

• Published in: Journal of carbohydrate chemistry Vol. 23; no. 5; pp. 325 - 335
• Main Authors: Taboada, Lidcay Herrera, Feist, Holger, Suarez, Jose Quincoces, Michalik, Manfred, Peseke, Klaus
• Format: Journal Article
• Language: English
• Published: 01.12.2004
• DOI: 10.1081/CAR-200035736
• ISSN: 0732-8303

1-(Methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-a-D-altropyranosid-2-yl)-4-ph enyl-but- 3-yn-2-one (4) was synthesized by the reaction of (methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-a-D-altropyranosid-2-yl)ethan al (2) with lithium phenylethynide and following oxidation. Compound 4 and hydrazine hydrate provided the 3(5)-(methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-a-D-altropyranosid-2-yl-methy l)-5(3)-p henyl-1H-pyrazole (5). The reactions of 4 with amidinium salts and a S-methyl-isothiouronium salt, respectively, furnished the pyrimidine C-nucleoside analogues 6a-6c. Treatment of 4 with 2-aminobenzimidazole afforded 2-(methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-a-D-altropyranosid-2-ylmethyl )-4-pheny l-benzo [4,5]imidazo[1,2-a]pyrimidine (7a). Compound 4 and sodium azide yielded 2-(methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-a-D-altropyranosid-2-yl)-1-[5 (4)-pheny l-1H(2H)-1,2,3-triazole-4(5)-yl]ethanone (8).