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Preparation of new c nucleotides by intra molecular dehydration of 2 penta hydroxypentyl 4 5 6 7 tetra hydro indol 4 ones


Carbohydrate Research 80(1): 37-44
Preparation of new c nucleotides by intra molecular dehydration of 2 penta hydroxypentyl 4 5 6 7 tetra hydro indol 4 ones
Acid-catalyzed dehydration of the polyhydroxyalkyl chain of 6,6-dimethyl-2-(D-gluco-pentitol-1-yl)-4,5,6,7-tetrahydroindol-4-one and of 6,6-dimethyl-2-(D-manno-pentitol-1-yl)-4,5,6,7-tetrahydroindol-4-one gave 2-.alpha.-D-arabinofuranosyl-6,6-dimethyl-4,5,6,7-tetrahydroindol-4-one. Similarly, 2-.beta.-D-lyxopyranosyl-6,6-dimethyl-4,5,6,7-tetrahydroindol-4-one and 2-.beta.-D-lyxopyranoxyl-4,5,6,7-tetrahydroindol-4-one were obtained by dehydration of 6,6-dimethyl-2-(D-galacto-pentitol-1-yl)-4,5,6,7-tetrahydroindol-4-one and 2-(D-galacto-pentitol-1-yl)-4,5,6,7-tetrahydroindol-4-one, respectively. The structures of the new C-nucleosides described were elucidated by chemical and physical methods.


Accession: 006173572



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