Abstract
(Z)- and (E)- isomers of oct-2,6-dienopyranosiduronates have been synthesized in a completely stereoselective manner from ethyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside. The selectivity of the processes is dictated by an unexpected opposite stereochemical behavior towards stabilized Wittig ylides of protected and unprotected 4-hydroxy derivatives in hex-2-enopyranoside-6-aldehydes.
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