T. Sakakibara, R. Sudoh
Sep 1, 1976
Citations
0
Influential Citations
5
Citations
Journal
Carbohydrate Research
Abstract
Abstract Treatment of methyl 4,6- O -benzylidene-2,3-dideoxy-3-nitro-β- D - erythro -hex-2-enopyranoside ( 2 ) with nitrous acid afforded the title 2-nitro sugar ( 4 ). The same product was also prepared by heterogeneous reaction of methyl 2- O -acetyl-4,6- O -benzylidene-3-deoxy-3-nitro-β- D -glucopyranoside ( 1 ) with sodium nitrite in the presence of a phase-transfer catalyst. Acid hydrolysis of 4 gave methyl 2-deoxy-2-nitro-β- D -glucopyranoside ( 7 ). Acetylation of 4 , followed by elimination of acetic acid, afforded a 2-nitroalkene ( 6 ). 71e 3-acetate 5 reacted with ammonia, dimethylamine, and 2,4-pentanedione to give the products 8 , 9 , and 10 , respectively, having the gluco configuration.