Re: ORGLIST: aldose oxidation

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From: John Deutsch (deutschj$##$essex.UCHSC.edu)
Date: Tue Jan 19 1999 - 18:41:51 EST


I am interested in gently oxidizing an aldose to the corresponding
keto-acid. For example

CHO CO2H
CHOH CO
CHOH to CHOH
CHOH CHOH
CHOH CHOH
CH2OH CH2OH

I don't want to disturb the steriochemistry at positions 3-5.
I plan on forming an osazone and then the osone- and then oxidize the
aldehyde- preferably in a system in which I don't use metal ions for
oxidation. Does anyone have experience, or know where I can find some
references for this type of work? I assume this was all done well in the
late 19th century by Emil Fischer.

John Deutsch

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