92574-10-2

Basic information

• Product Name: 5-deoxy-D-threo-hex-2-ulose
• CAS NO: 92574-10-2
• Molecular Weight: 164.158
• Mol File: 92574-10-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 5-deoxy-D-threo-hex-2-ulose(CAS DataBase Reference)
• NIST Chemistry Reference: 5-deoxy-D-threo-hex-2-ulose(92574-10-2)
• EPA Substance Registry System: 5-deoxy-D-threo-hex-2-ulose(92574-10-2)

Safety Data

• Hazardous Substances Data: 92574-10-2(Hazardous Substances Data)

Upstream product

• 20847-11-4 2-deoxy-D-glucitol 
• 1113-60-6 3-hydroxy-2-oxopropionic acid 
• 143106-66-5 3-Deoxy-DL-glycero-tetrose 
• 154-17-6 D-2-deoxyglucose 

Downstream Products

• 250128-96-2 5-deoxy-D-psicose 
• 92583-49-8 D-xylo-5-deoxy-hexose 

Relevant articles and documents

A concise approach to the synthesis of all twelve 5-deoxyhexoses: d-tagatose-3-epimerase-a reagent that is both specific and general

2-Deoxy-d-glucitol and 2-deoxy-d-allitol, both prepared as crystalline polyols from d-erythronolactone, are oxidized by Gluconobacter thailandicus NBRC 3254 to 5-deoxy-d-threo-hexulose [5-deoxy-d-fructose = 5-deoxy-l-sorbose] and 5-deoxy-d-erythro-hexulose [5-deoxy-l-psicose = 5-deoxy-d-tagatose], respectively. d-Tagatose-3-epimerase (DTE) equilibrates 5-deoxy-d-fructose to 5-deoxy-d-psicose and 5-deoxy-l-psicose to 5-deoxy-l-fructose, providing substrates for the preparation of all eight d- and l-5-deoxy aldohexoses by aldose isomerases. This combination of chemical and biotechnological methods allows a concise approach to the synthesis of all twelve 5-deoxy hexoses and further demonstrates the range of deoxy sugar substrates on which DTE is active. NMR studies show that 5-deoxy-d-fructose exists solely as the β-pyranose form whereas both pyranoses of 5-deoxy-d-fructose [α:β. 22:78] are observed. [For the sake of clarity, all ketoses in this Letter are shown in blue, alditols in red and aldoses in purple.].

ENZYMATIC ALDOL REACTION/ISOMERIZATION AS A ROUTE TO UNUSUAL SUGARS

Utilizing fructose diphosphate aldolase and glucose isomerase as catalysts, 3-, 5-, and 6-deoxy- and 6-O-methylhexoses have been synthesized from dihydroxyacetone phosphate or acetol phosphate and the corresponding hydroxypropionaldehydes.