Reaction conditions are described for the chain extension of 2,3 : 5,6-di-O-isopropylidene-D-mannose (1) with a Wittig ylide (2) to give the acyclic manno-octenoate (3) or the C-glycofuranosides (4 and 5) and with the Knoevenagel-Doebner reaction to afford the isomeric gluco-octenoate (6); the isomerisation proved to occur in the latter reaction provides an explanation for an anomaly in the literature and indicates that the C-glycosides (4 and 5) are formed by a Michael-type ring closure rather than via a betaine intermediate.
|Number of pages||2|
|Journal||Journal of the Chemical Society, Chemical Communications|
|Publication status||Published - 1982 Jan 1|
ASJC Scopus subject areas
- Molecular Medicine