78029-00-2

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 161453-17-4 tert-butyl (3R,αR)-3--2-oxo-3-phenylpropionate 
• 1454771-29-9 tert-butyl (R,R)-2-methanesulfonyloxy-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoate 
• 1454771-27-7 tert-butyl (R,R)-2-hydroxy-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoate 
• 14990-09-1 tert-butyl cinnamate 
• 1454771-48-2 (4S,5R)-5-phenyl-4-(tert-butoxycarbonyl)-N⁽³⁾-(tert-butoxycarbonyl)oxazolidin-2-one 
• 1454771-50-6 (4S,5R)-5-phenyl-4-(tert-butoxycarbonyl)oxazolidin-2-one 
• 151671-03-3 tert-butyl (2R,3R,αR)-3--2-hydroxy-3-phenylpropionate 
• 1454771-37-9 di-tert-butyl (2S,3R)-3-phenylaziridine-N⁽¹⁾,2-dicarboxylate 
• 1454771-35-7 tert-butyl (2S,3R)-2-methanesulfonyloxy-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoate 
• 1454771-33-5 tert-butyl (2S,3R)-2-hydroxy-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoate 

Downstream Products

• 6254-48-4 (2S,3R)-3-phenylserine 
• 1263322-08-2 C₁₃H₁₉NO₃ 

Relevant academic research and scientific papers

Asymmetric Total Synthesis and Evaluation of Antitumor Activity of Ophiorrhisine A and Its Derivatives

The first asymmetric total synthesis of ophiorrhisine A (1), a new cyclic tetrapeptide isolated from Ophiorrhiza nutans, was accomplished via an intramolecular aromatic nucleophilic substitution reaction (IMSNAr) of a linear tripeptide to construct a 14-membered paracyclophane ring, resulting in confirmation of its structure and absolute configuration. The structure-activity relationship study of 1 and its derivatives demonstrated that some derivatives possessed cytotoxicity toward human cancer cell lines A549, HT29, and HCT116.

Trading N and O: Asymmetric syntheses of β-hydroxy-α-amino acids via α-hydroxy-β-amino esters

Both diastereoisomers of 2-amino-3-hydroxybutanoic acid and 2-amino-3-hydroxy-3-phenylpropanoic acid have been prepared from enantiopure α-hydroxy-β-amino esters via the intermediacy of the corresponding cis- and trans-aziridines. Aminohydroxylation of two α,β-unsaturated esters produced enantiopure 2,3-anti-α-hydroxy-β-amino esters in >99:1 dr. Subsequent epimerisation at the C(2)-position via a sequential oxidation/diastereoselective reduction protocol gave the corresponding enantiopure 2,3-syn-α-hydroxy-β-amino esters in >99:1 dr. These syn- and anti-substrates were then converted into the corresponding N-Boc protected cis- and trans-aziridines, respectively, via a three step reaction sequence: (i) hydrogenolysis and in situ N-Boc protection; (ii) OH-activation; and (iii) aziridine formation. Subsequent regioselective ring-opening of the C(3)-methyl-aziridines with Cl3CCO2H proceeded with inversion of configuration to give the corresponding 2-amino-3-trichloroacetate esters, whereas the analogous reaction with the C(3)-phenyl-aziridines resulted in rearrangement to the corresponding oxazolidin-2-ones with retention of configuration. In each case, hydrolysis of the products from these ring-opening reactions produced the corresponding enantiopure β-hydroxy-α-amino acids as single diastereoisomers.