G. Lourens
Mar 1, 1971
Citations
0
Influential Citations
13
Citations
Journal
Carbohydrate Research
Abstract
Abstract The addition of nitromethane to 1,2- O -isopropylidene-5- O -trityl-α- D - erythro -pentofuranos-3-ulose ( 1 ) and to the corresponding 5- O-p -tolylsulfonyl compound 2 to give branched-chain sugars 3 and 4 is described. The D - ribo configuration for 4 was established by reduction, followed by acetylation, to give 3- O -acetyl-5,1′-acetyl- epimino-5-deoxy-1,2- O -isopropylidene-3- C -methyl-α- D -ribofuranose ( 5 ). Acetylation of 3 and 4 , followed by base-catalyzed elimination of acetic acid, gave the corresponding nitro-olefins 9 and 8 (not isolated). Reduction of 8 with sodium borohydride readily gave 3-deoxy-1,2- O -isopropylidene-3- C -nitromethyl-5- O-p -tolylsulfonyl-α- D -ribofuranose ( 10 ). Catalytic hydrogenation of 10 , followed by benzoylation, gave the 3- C -benzamidomethyl compound 12 in 78% yield. 3- C -Acetamidomethyl-5- O -acetyl-3-deoxy-1,2- O -isopropylidene-α- D -ribofuranose ( 13 ) was similarly prepared from the nitro-olefin 9 . The 3-deoxy- D - ribo configuration for compounds 10 , 11 , 12 , and 13 was established by n.m.r. spectroscopy.