SYNTHESIS OF 1,5-LACTONES OF 3-DEOXY-D-manno-2-OCTULOPYRANOSONIC ACID ( KDO)

Article abstract of DOI:10.1016/0008-6215(88)84114-4

An unambigous synthesis of methyl 3-deoxy-α-D-manno-2-octulopyranosidono-1,5-lactone from methyl (methyl 3-deoxy-α-D-manno-octulopyranosid)onate via the 7,8-O-isopropylidene derivative is described.Treatment of the 4,5-stannylene derivative of this acetal with benzyl bromide gave the 1,5-lactone from which the protecting groups were removed.The acetylated 1,5-lactone was produced by acetylation of ammonium 3-deoxy-D-manno-2-octulosonate or treatment of the pyridinium salt with dicyclohexylcarbodi-imide and acetylation.No lactone was produced when only HO-7 was unsubstituted.When treated with an excess of 2-methoxypropene, methyl (methyl 3-deoxy-α-D-manno-2-octulopyranosid)onate afforded the 4,5:7,8-di-O-isopropylidene derivative, from which the 7,8-acetal group could be removed selectively.