1.2- Epoxy-3-alkanols

A simple epoxy alkanol to begin with is 1,2-epoxyhexan-3-ol (10.47), which has been postulated as a metabolite of the air pollutant hex-l-ene (10.46). This compound was found to be a good substrate for rat liver microsomal EH, yielding hexane-1,2,3-triol (10.48) [127], 1,2-Epoxyhexan-3-ol contains two stereogenic centers and exists as four stereoisomers that were hydrated at different rates, in the order (2S,3R)-erythro > (2S,3S)-threo > ( 2R,3S)-erythro > (2R,3R)-threo. In other words, the metabolic hydrolysis of this substrate is not influenced by the configuration at C(3), but clearly by that at C(2), with the (25)-epimers being better substrates than the (2/7)-cpi-... 

In epoxy alkanols that carry two functional groups separated by a further C-atom, the OH group did not interfere significantly with EH-catalyzed hydrolysis. This was seen with l,2-epoxyheptan-4-ol and 3,4-epoxyhexan-l-ol [128]. The OH group, however, did enhance the bioalkylating potential of even aliphatic epoxides. 

Epoxy-alkanol >240h 240h Slow degradation of cross-linker 28,31... 

Epoxy-alkanol amine adduct Reaction product of diethanol amine with DGEBA MW = ca. 580 f - 6 r = 1.7. 

An alternative synthetic method for preparing chiral l,2-epoxy-3-alkanol tosylates using Sharpless AD reaction as the key step has been reported and was used in the total synthesis of two insect pheromones namely,... 

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