Investigations in the fie ld of substituted furanurona ldehydes steric directivity of the nitromethane condensation
Summary1. The condensation of the anomeric methyl 2,3-di-O-benzyl-D-xylofuranosiduronaldehydes with nitromethane has been studied.2. It has been shown that the position of the substituent at the glycosidic center has an influence on the steric directivity of this reaction.3. The structure of the 6-nitro-6-deoxyhexofuranosides synthesized has been confirmed by their conversion into known derivatives of methyl D-glucofuranosides.
Nitromethane-Condensation Reaction with 5-Aldehydes of Pentodialdofuranosides
Treatment of methyl 2, 3-di-O-benzyl-α-L-arabino-pentodialdo-1, 4-furanoside (1) with nitromethane in the presence of sodium methoxide afforded an epimeric mixture of methyl 2, 3-di-O-benzyl-6-deoxy-6-nitro-α-L-altro-(2c) and -β-D-galactofuranoside (3c) in a ratio of 2.5 : 1. On the other hand, the analogous treatment of 3-O-benzyl-1, 2-O-isopropylidene-α-D-xylo-pentodialdo-1, 4-furanose (7b) with nitromethane gave 3-O-benzyl-6-deoxy-1, 2-O-isopropylidene-6-nitro-α-D-glucofuranose (8b) predominantly.
THE SYNTHESIS OF ACETAMIDO-DEOXY KETOSES BY ACETOBACTER SUBOXYDANS: PART II
The microbiological oxidation of 2-acetamido-2-deoxy-D-glucitol by Acetobacter suboxydens yielded a crystalline ketose which is shown to be 5-acetamido-5-deoxy-L-xylohexulose.