132409-53-1

Upstream product

• 115936-21-5 (Z)-(4S,5R)-ethyl 6-(benzyloxy)-4,5-epoxy-4-methyl-2-hexenoate 
• 115827-29-7 (E)-(4S,5R)-ethyl 6-(benzyloxy)-4,5-epoxy-4-methyl-2-hexenoate 
• 115827-30-0 (Z)-3-((2R,3R)-3-Benzyloxymethyl-2-methyl-oxiranyl)-prop-2-en-1-ol 
• 115936-20-4 [(2S,3R)-3-[(benzyloxy)methyl]-2-methyloxiran-2-yl]methanol 
• 100-39-0 benzyl bromide 
• 60656-87-3 benzyloxyacetoaldehyde 
• 622-08-2 2-Benzyloxyethanol 
• 115936-22-6 (Z)-(4S,5R)-6-(benzyloxy)-4,5-epoxy-4-methyl-2-hexen-1-ol 
• 132409-59-7 (E)-(4R,5R)-6-(Benzyloxy)-4,5-epoxy-4-methyl-1-<(methylthio)methoxy>-2-hexene 
• 132409-59-7 (Z)-(4R,5R)-6-(Benzyloxy)-4,5-epoxy-4-methyl-1-<(methylthio)methoxy>-2-hexene 
• 917-54-4 methyllithium 
• 115827-31-1 (E)-(4S,5R)-6-(benzyloxy)-1-<(tert-butyldimethylsilyl)-oxy>-4,5-epoxy-4-methyl-2-hexane 
• 115827-31-1 (Z)-(4S,5R)-6-(benzyloxy)1-<(tert-butyldimethylsilyl)-oxy>-4,5-epoxy-4-methyl-2-hexane 
• 115827-30-0 (E)-(4S,5R)-6-(benzyloxy)-4,5-epoxy-4-methyl-2-hexenol 

Relevant academic research and scientific papers

Diastereodifferentiation in SN2' Additions of Methylcuprates to Nonracemic Acyclic Vinyloxiranes

SN2' additions of Me2CuLi, MeCu(CN)Li, and Me2Cu(CN)Li2 to the 2S and 2R alkoxy cis-(Z)- and -(E)-vinyloxiranes 8, 9, 13, and 14 were examined as possible routes to acyclic subunits of polypropionate natural products.Highest anti:syn ratios wer

Stereochemistry of SN2' Additions to Acyclic Vinyloxiranes

The isomeric trans-(E)-, trans-(Z)-, cis-(E)-, and cis-(Z)-vinyloxiranes 7,9,17 and 19 were prepared from 2-(benzyloxy)ethanol by sequential Swern-Wittig or Swern-Horner-Emmons propionate condensation, DIBAH reduction, Sharpless epoxidation, Swern oxidation, Wittig or Horner-Emmons acetate condensation, and a second DIBAH reduction.Addition of lithium dimethylcuprate and lithium methylcyanocuprate to these epoxides in THF-eather at -20 to 0 deg C afforded the allylic alcohols 22,25, ent-23, and ent-22 as the major products.These products are formed by anti addition to the lower energy conformer (s-trans for 7,17, and 19 and s-cis for 9) of the respective vinyloxirane.The conformational preferences of transition-state-like geometries of the vinyl-oxiranes, calculated with the aid of Still's MACROMODEL program, were in agreement with the observed trends.