ORGLIST: Alkylglycosides

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From: Manuel Toennis (Manuel.Toennis$##$ch.tum.de)
Date: Tue Dec 15 1998 - 09:05:19 EST


Hello,

can anyone out there help me with the synthesis of
alkylglycosides / -maltosides ?

The classic 'koenigs-knorr' method yields as main product only the
orthoesther.
Now, someone told me that there is a method starting directly from
the pentaacetylglucose, but he did not know any more details.
Litrature search could not give a hint, so do you know a method for:

Ac5-Glu + ROH -> Ac4-Glu-OR + HOAc
Ac8-Mal + ROH -> Ac8-Mal-OR + HOAc
      ^ ^
(alpha/beta ?) (alpha/beta ?)

I really need the (final) Detergents to solublise some Proteins
for NMR Measurements and the commercially avilable Detergents are not
suitable for my purposes.
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