75347-13-6

Upstream product

• 129413-14-5 O,O-isopropylidene-(-)-bursatellin 
• 119-62-0 D-threo-2-amino-1(4-nitrophenyl)-1,3-propanediol 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 1350705-71-3 C₁₈H₃₀N₂O₃Si 
• 1350705-68-8 ethyl (2S,3R)-3-(4-(benzyloxy)phenyl)-2-((tert-butoxycarbonyl)amino)-3-hydroxypropanoate 
• 1350705-81-5 (2S,3R)-ethyl 3-(4-(benzyloxy)phenyl)-2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)propanoate 
• 1350705-69-9 ethyl (2S,3R)-2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)-3-(4-hydroxyphenyl)propanoate 
• 1350705-83-7 ethyl (2S,3R)-2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)-3-(4-(2-cyanoethoxy)phenyl)propanoate 
• 1350705-70-2 tert-butyl (1R,2R)-1-(tert-butyldimethylsilyloxy)-1-(4-(2-cyanoethoxy)phenyl)-3-hydroxypropan-2-ylcarbamate 
• 1350705-85-9 N-((1R,2R)-1-(tert-butyldimethylsilyloxy)-1-(4-(2-cyanoethoxy)-phenyl)-3-hydroxypropan-2-yl)formamide 
• 123-08-0 4-hydroxy-benzaldehyde 
• 104315-07-3 (E)-ethyl 3-(4-(benzyloxy)phenyl)acrylate 
• 51458-27-6 N-[(1R,2R)-2-(4-Amino-phenyl)-2-hydroxy-1-hydroxymethyl-ethyl]-formamide 
• 23885-67-8 N-[(1R,2R)-2-Hydroxy-1-hydroxymethyl-2-(4-nitro-phenyl)-ethyl]-formamide 

Downstream Products

• 129413-12-3 (2R,3R)-2-formylamino-3-(4-hydroxyphenyl)-1,3-propanediol 

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.

A synthesis of (-)-bursatellin

A synthesis of (-)-bursatellin has been accomplished by an application of a new procedure for oxidation at a benzylic position with K2S2O8 to 1-acetoxy-2(S)-N-Boc-amino-3-(4-benzyloxyphenyl) propane as a key step.

Stereochemistry and Synthesis of Bursatellin from Chloramphenicol

The 1R,2R stereochemistry for (-)-bursatellin has been established by synthesis from chloramphenicol D-base.