Toward the synthesis of fine chemicals from lactose: preparation of D-xylo and L-lyxo-aldohexos-5-ulose derivatives.

نویسندگان

  • Giorgio Catelani
  • Felicia D'Andrea
  • Lorenzo Guazzelli
  • Venerando Pistarà
چکیده

The transformation of (5R)-2,6-di-O-benzyl-5-C-methoxy-beta-D-galactopyranosyl-(1-->4)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal (8) into partially protected derivatives of D-xylo- and L-lyxo-aldohexos-5-ulose has been reported, applying appropriate epimerisation methods to its 3'-O- and 4'-O-protected alcoholic derivatives.

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Useful access to enantiomerically pure protected inositols from carbohydrates: the aldohexos-5-uloses route

The intramolecular aldol condensation of aldohexos-5-ulose derivatives of the D-xylo and L-ribo stereoseries has been studied. Only one of the four possible inososes was isolated from both stereoseries in reasonable yields (30-38%). The results obtained, together with the previous findings for the L-arabino and L-lyxo stereoseries, allowed for the rationalisation of a mechanism of the reaction ...

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عنوان ژورنال:
  • Carbohydrate research

دوره 344 6  شماره 

صفحات  -

تاریخ انتشار 2009