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Wednesday, August 03, 2005

Reduction of Aldehyde to an Alcohol -- Synthesis of D,L-1,2,4-butanetriol

D,L-1,2,4-butanetriol can be made in two different ways; the first way is commercial synthesis through reduction of esterified D,L-malic acid with sodium borohydride, NaBH4, while the second way involves microbes. The latter method was the focus of the journal article. Nitration of racemic D,L-1,2,4-butanetriol results in D,L-1,2,4-butanetriol trinitrate, a compound that is the energetic equivalent of nitroglycerin, but is less shock sensitive, more thermally stable, and less volatile. One of the final steps in the synthesis of D, L-1,2,4-butanetriol via microbes is the reduction of a racemic mixture of D,L-3,4-dihydroxybutanal (aldehyde), to the final alcohol product, as seen in the reaction below. The catalyst for the reaction is dehydrogenase from E. coli.

For the full text of this article, click on the following link (and then the second listed link in citeulike):
Article Link.

5 Comments:

  • Full Marks. It is interesting that you mention that the alternative synthesis involves reduction of an ester with borohydride. Normally borohydride won't reduce esters. What conditions are they using to make this possible?

    By Blogger Jean-Claude Bradley, at 2:33 PM  

  • I read that if sodium borohydride is combined with methanol (or even water) it becomes an even stronger reductant. The stronger conditions allow for reduction of esters, instead of just aldehydes and ketones.

    By Blogger shailja, at 11:00 AM  

  • Where did you read about increased borohydride activity in methanol?

    By Blogger Jean-Claude Bradley, at 7:28 AM  

  • There was a lot of information on sodium borohydride and other metal hydrides on the Rohm and Haas synthesis technologies website. here's the link to the slide show that i read about increased reductant activity:

    http://www.rohmhaas.com/hydride/safety_files/frame.htm#slide0118.htm

    By Blogger shailja, at 10:26 AM  

  • Thanks - you just taught me something useful

    By Blogger Jean-Claude Bradley, at 10:32 AM  

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