D-Altrose – general description and application

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General description of D-Altrose:

D-Altrose [1990-29-0] or (2S,3R,4R)-2,3,4,5,6-pentahydroxyhexanal is an aldohexose monosacharid, C-3 epimer of mannose. The pure compound is a colorless to offwhite crystalline solid with a melting point of 103-105 °C and a rotation at equilibrium [α] +32.6° in water.^[1] It is an unnatural monosacharide that is soluble in water and almost insoluble in methanol.

D-Altrose can be prepared from levoglucosenone via D-altrosan, formed after stereoselective reduction and cis-hydroxylation.^[2] D-altrose is formed as byproduct in the production of D-allose from D-psicose via epimerization catalysed with L-rhamnose isomerase.^[3] Can be prepared from D-fructose using a combination of the immobilized D-tagatose 3-epimerase and D-arabinose isomerase but only with 6% overall yield.^[4]

Application of D-Altrose:

D-altrose is used in synthesis of various unnatural analogues of biological active compounds like iminosugars.^[5] Due to the lack of industrial production, application of D-altrose in different areas of research is still limited.

Product categorization (Chemical groups):

Main category:

• Alcohols / Phenols / Hydroxy compounds
• Sugar derivatives

Second level:

• Aliphatic

Third level:

• Heterocyclic compounds

Regulatory Information:

• Not a hazardous substance or mixture according to Regulation (EC) No 1272/2008

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