2817-48-3Relevant academic research and scientific papers
PROCESS FOR PRODUCING 2-DEOXYALDOSE COMPOUND
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Page/Page column 11-12, (2008/06/13)
An object of the present invention is to provide a method for preparing 2-deoxyaldoses on industrial scale in which the yield or the volumetric efficiency is excellent and the operation is simple, as compared to the conventionally known preparation method.A compound represented by the general formula (1) such as 2-keto-3-deoxygluconic acid or the like is reduced by the catalytic hydrogenation method using a metal such as palladium or the like, or a compound represented by the general formula (1) such as 2-keto-3-deoxygluconic acid or the like is reduced by using a hydride reducing agent in a solvent of not more than 30 weight times the amount of the above compound, for synthesizing 2-keto-3-deoxyaldonic acid. The 2-keto-deoxyaldonic acid was decarboxylated to obtain 2-deoxyaldoses.The method of the present invention is economical and efficiently excellent.
Preparation of 3-Deoxy-aldonolactones by Hydrogenolysis of Acetylated Aldonolactones
Bock, Klaus,Lundt, Inge,Pedersen, Christian
, p. 155 - 162 (2007/10/02)
Acetylated aldono-1,4-lactones, when treated with hydrogen in the presence of triethylamine and palladium on carbon, form acetylated 3-deoxy-aldono-1,4-lactones in high yield through elimination of the 3-acetoxy group and subsequent stereospecific hydrogenation of the unsaturated intermediate.Thus, acetylated D-galactono-1,4-lactone (1) yields tri-O-acetyl-3-deoxy-D-xylo-hexono-1,4-lactone (3a).Acetylated D-mannono- or D-glucono-1,4-lactone both give 3-deoxy-D-arabino-hexono-1,4-lactone (10a), whereas the four acetylated D-pentono-1,4-lactones (14-17) all afford di-O-acetyl-D-threo-pentono-1,4-lactone (18a).D-Gluconolactone can be converted into (R)-γ-caprolactone (27) on treatment with hydrogen bromide followed by a series of reductions.Similarly, D-lyxonolactone produces 2,3-dideoxy-D-glycero-pentono-1,4-lactone (29).
