50480-80-3

Upstream product

• 32443-72-4 D-erythro-3-deoxy-[2]hexosulose-bis-phenylhydrazone 
• 93857-40-0 sodium 3-deoxy-D-mannonate 
• 61259-48-1 2,3,4,6-tetra-O-acetyl-D-glucono-1,5-lactone 
• 17510-99-5 4,5,6-trihydroxy-2-oxohexanoic acid 

Downstream Products

• 499-87-6 3-deoxy-D-ribo-hexono-1,4-lactone 
• 533-67-5 2-Deoxy-D-ribose 
• 284031-19-2 3-deoxy-1,2-O-isopropylidene-6-O-tosyl-β-D-arabino-hexofuranose 
• 284031-37-4 1,3,6-trideoxy-1,6-imino-D-arabino-hexitol 

Relevant academic research and scientific papers

PROCESS FOR PRODUCING 2-DEOXYALDOSE COMPOUND

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.

Production of aldoses

An aldose having n-1 carbon atoms is produced from an aldonic acid having n carbon atoms using hypochlorous acid or a hypochlorite in a high yield at low cost with safety, by treating the reaction mixture with a compound having reactivity with the hypochlorous acid or hypochlorite higher than that with the produced aldose.

FORMATION OF GLUCOMETASACCHARINOLACTONES IN THE PYROLYSIS OF CURDLAN, A (1->3)-β-D-GLUCAN

The volatile products of vacuum pyrolysis of curdlan are very much influenced by the presence of small proportions of sodium chloride in the polysaccharide during pyrolysis.In the absence of contamination by this salt, the major, volatile products are the 1,6-anhydro-D-glucoses (pyranose and furanose) in 49percent yield.Addition of increasing proportions of sodium chloride decrases the yield of these anhydro-D-glucoses, and causes formation of increasing proportions of 3-deoxy-D-ribo-hexono-1,4-lactone and its D-arabino epimer (i.e., the glucometasaccharinolactones ) in a combined yield of up to 38percent.It is concluded that the pyrolysis of (1->3)-glycans can lead to a peeling reaction of the same type as that already known for alkaline degradation.The effect of other salts was also studied.

Preparation of 3-Deoxy-aldonolactones by Hydrogenolysis of Acetylated Aldonolactones

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).