sucrose reaction

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Joseph DeSousa - 14 Oct 2005 08:45 GMT

Hello,

I am attempting to graft a primary alcohol on to the a disaccharide (sucrose) via a etherification reaction in the presence of an acid catalyst. The challenge is finding an appropriate acid...I've used sulfonic acid, organic diacids, and phosphoric acids with varying degrees of success. Does any know a catalyst that would effective work here and what would be a acceptable solvent (other than aqueous) for this reaction. Thanks for time.

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Joseph DeSousa

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muha - 17 Oct 2005 09:10 GMT

This is a dumb idea what you are trying to do. The glycosidic bond will
be long gone. Your sugars will dehydrate into ketonic products and
polymers.

You need to use basic conditions and an alkylating agent like alkyl
iodide.

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Al - 17 Oct 2005 09:10 GMT

Why are you using acidic conditions for this transformation? Is the
acetal of the sucrose not going to decompose under such conditions?

> Hello,
>
> I am attempting to graft a primary alcohol on to the a disaccharide (sucrose) via a etherification reaction in the presence of an acid catalyst. The

challenge is finding an appropriate acid...I've used sulfonic acid, organic
diacids, and phosphoric acids with varying degrees of success. Does any know a
catalyst that would effective work here and what would be a acceptable solvent
(other than aqueous) for this reaction. Thanks for time.

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oxazoline - 14 Nov 2005 09:12 GMT

If there're reasons you can't run these in water or an exces of the
alcohol, you may want to use a non-polar solvent and a PTC. THF or
dioxane might be appropriate. How high an alcohol(s)? what acids?
Have you tried Zn?

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Natural Science Forum / Chemistry / Organic Synthesis / November 2005

sucrose reaction