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Syntheses of biologically important carbohydrates 35. synthesis of exocyclic saccharide enol ethers and their reaction to branched chain carbohydrates



Syntheses of biologically important carbohydrates 35. synthesis of exocyclic saccharide enol ethers and their reaction to branched chain carbohydrates



Liebigs Annalen der Chemie (4): 613-624



Wittig olefination of the 3-uloses 1 and 9 leads to the exocyclic (E)- and (Z)-enol ethers 2 and 3 or 11 and 10, respectively. On cis-hydroxylation these are uniformly transformed into the hydroxyformy-branched gluco derivatives 4 and 8, respectively. Acidolysis of 2a as well as mercuri or iodo hydroxylation with subsequent reduction give the 3-C-formyl-branched sugars 12 and 13. Alternatively, the latter may also be obtained by treatment of the ulose 1 with tosylmethyl isocyanide via the cyano-branched compound 16. Addition of iodine/silver isocyanate to 2a and subsequent methanolysis gives the epimeric 3-deoxy-3-iodo-3'-aminals 14 and 15 which on treatment with base yield the substituted aziridine 17 or the branched olefin sugar derivative 18, respectively.

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