671232-58-9

Upstream product

• 917-64-6 methyl magnesium iodide 
• 671232-57-8 (E)-5-(4-methoxy-benzyloxy)-pent-2-en-1-al 
• 172427-68-8 ethyl <2E>-5-(4-methoxybenzyloxy)-2-pentenoate 
• 128461-65-4 3-(p-methoxybenzyloxy)propanal 

Downstream Products

• 671232-68-1 tert-Butyl-((S)-1-{(2R,3S)-3-[2-(4-methoxy-benzyloxy)-ethyl]-oxiranyl}-ethoxy)-dimethyl-silane 
• 671232-59-0 (S)-1-{(2S,3S)-3-[2-(4-Methoxy-benzyloxy)-ethyl]-oxiranyl}-ethanol 

Relevant academic research and scientific papers

Regio- and stereoselective SN2′ reaction of an allylic picolinate in the synthesis of LY426965

Allylic substitution of secondary γ,γ-disubstituted allylic picolinates with ArMgBr-based copper reagents was applied to the synthesis of LY426965. Reduction of (R)-6-(PMB-oxy)-3-hexyn-2-ol of 93% ee (PMB = p-MeOC6H4CH2) using Red-Al gave (R,Z)-4-iodo-5-(PMB-oxy)hex-3-en-2-ol, which was later converted to the Me-substituted allylic picolinate by Pd-catalyzed coupling with MeZnI followed by esterification with picolinic acid. Allylic substitution with PhMgBr/Cu(acac)2 proceeded with high anti SN2′ selectivity (99%). Ozonolysis, addition of c-Hex-MgBr to the resulting aldehyde, and reductive amination with the piperazine derivative afforded LY426965.

Synthesis of chiral 4-hydroxy-2,3-unsaturated carbonyl compounds from 3,4-epoxy alcohols by oxidation: Application in the formal synthesis of macrosphelide A

An interesting transformation during the oxidation of 3,4-epoxy alcohols 1a-d, derived from the corresponding homoallylic alcohols, led to the formation of 4-hydroxy-2,3-unsaturated carbonyls 2a-d in very good yields. One of these products 2c was transfor