1350705-70-2

Upstream product

• 104315-07-3 (E)-ethyl 3-(4-(benzyloxy)phenyl)acrylate 
• 123-08-0 4-hydroxy-benzaldehyde 
• 1350705-83-7 ethyl (2S,3R)-2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)-3-(4-(2-cyanoethoxy)phenyl)propanoate 
• 1350705-69-9 ethyl (2S,3R)-2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)-3-(4-hydroxyphenyl)propanoate 
• 1350705-81-5 (2S,3R)-ethyl 3-(4-(benzyloxy)phenyl)-2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)propanoate 
• 1350705-68-8 ethyl (2S,3R)-3-(4-(benzyloxy)phenyl)-2-((tert-butoxycarbonyl)amino)-3-hydroxypropanoate 
• 4397-53-9 p-benzyloxybenzaldehyde 

Downstream Products

• 1350930-48-1 oxazinin-5 
• 1350930-50-5 oxazinin-6 
• 1350705-77-9 3-(4-((R)-((3R,6R)-6-(1H-indol-3-yl)-5-oxomorpholin-3-yl)((tert-butyldimethylsilyl)oxy)methyl)phenoxy)propanenitrile 
• 1350705-88-2 3-(4-((R)-((3R,6S)-6-(1H-indol-3-yl)-5-oxomorpholin-3-yl)((tert-butyldimethylsilyl)oxy)methyl)phenoxy)propanenitrile 
• 1350705-71-3 C₁₈H₃₀N₂O₃Si 
• 1350705-85-9 N-((1R,2R)-1-(tert-butyldimethylsilyloxy)-1-(4-(2-cyanoethoxy)-phenyl)-3-hydroxypropan-2-yl)formamide 
• 1350705-72-4 N-((1R,2R)-1-((tert-butyldimethylsilyl)oxy)-1-(4-(2-cyanoethoxy)phenyl)-3-hydroxy propan-2-yl)-2-(1H-indol-3-yl)-2-oxoacetamide 
• 75347-13-6 N-{(1R,2R)-1-[4-(2-cyanoethoxy)phenyl]-1,3-dihydroxypropan-2-yl}formamide 

Relevant academic research and scientific papers

Enantioselective total syntheses and determination of absolute configuration of marine toxins, oxazinins

The enantioselective total syntheses of natural marine toxins, oxazinin-1, -2, -4, -5, -6 and linear precursor preoxazinin-7 are described. The synthetic highlights include Sharpless asymmetric aminohydroxylation and dihydroxylation, oxa-Michael reaction and intramolecular diastereoselective addition of an appropriate hydroxyl substituent to a 3-methyleneindolenine for the construction of the morpholine ring as key steps. The synthetic route also allowed the synthesis of the epi-preoxazinin and a structurally related secondary metabolite bursatellin isolated in 1980 from sea hare Bursatella leachii pleii and its epimer.

Asymmetric first total syntheses and assignment of absolute configuration of oxazinin-5, oxazinin-6 and preoxazinin-7

Asymmetric first total syntheses of the unprecedented toxins oxazinin-5, oxazinin-6 and preoxazinin-7 have been achieved from a common key intermediate 18, derived from a regiocontrolled Sharpless asymmetric aminohydroxylation and oxa-Michael reaction, which in addition to confirming the structure also established the absolute configuration of the natural products. On the way an expeditious synthesis of a metabolite bursatellin was completed in 8 steps. The Royal Society of Chemistry 2011.