The chemistry of D‐gluconic acid derivatives. Part IV Synthesis and reactions of some 2‐deoxy‐D‐hexonic acid derivatives, a new synthesis of 2‐deoxy‐D‐<i>arabino</i>‐hexose and some related compounds

Abstract

Abstract Treatment of methyl 3,4;5,6‐di‐ O ‐isopropylidene‐D‐gluconate ( 7 ) with triphenylphosphine/carbon‐tetrachloride/imidazole yields the corresponding 2‐chloro‐2‐deoxy‐D‐mannonate 8. The reduction of 8 under a variety of conditions led to a new synthesis of 2‐deoxy‐D‐glucose and some related acyclic compounds. The characterisation, and some reactions of the intermediate products, leading to chirally defined trihydroxy‐2‐alkenoates is also described.