137649-65-1

Upstream product

• 1152-62-1 Cbz-Met-OH 
• 56762-93-7 methyl (S)-2-(benzyloxycarbonylamino)-4-methylmercaptobutanoate 
• 1205674-06-1 (S)-benzyl {1-[methoxy(methyl)amino]-4-(methylthio)-1-oxobutan-2-yl}carbamate 
• 121421-45-2 N^α-benzyloxycarbonyl-L-methioninol 
• 2899-37-8 (S)-methioninol 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 137649-83-3 (4S,5R,4'S,5'R)-4,4'-Bis-(2-methylsulfanyl-ethyl)-3,3'-bis-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyl)-[5,5']bioxazolidinyl-2,2'-dione 
• 137764-57-9 (4S,5R,4'S,5'R)-4,4'-Bis-(2-methylsulfanyl-ethyl)-3,3'-bis-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyl)-[5,5']bioxazolidinyl-2,2'-dione 
• 137649-71-9 (3S,4R,5R,6S)-3,6-Bis-1,8-bis(methylthio)-4,5-octanediol 
• 121421-45-2 N^α-benzyloxycarbonyl-L-methioninol 

Relevant academic research and scientific papers

α-Amino Aldehydes as Readily Available Chiral Aldehydes for Rh-Catalyzed Alkyne Hydroacylation

Readily available α-amino aldehydes, incorporating a methylthiomethyl (MTM) protecting group on nitrogen, are shown to be efficient substrates in Rh-catalyzed alkyne hydroacylation reactions. The reactions are performed under mild conditions, employing a small-bite-angle bis-phosphine ligand, allowing for good functional group tolerance with high stereospecificity. Amino aldehydes derived from glycine, alanine, valine, leucine, phenylalanine, isoleucine, serine, tryptophan, methionine, and cysteine were successfully employed, as was an enantiomerically enriched α-OMTM-aldehyde derived from phenyllactic acid. The synthetic utility of the α-amino enone products is demonstrated in a short enantioselective synthesis of the natural product sphingosine.

Pinacol cross coupling of 2-[N-(alkoxycarbonyl)amino] aldehydes and aliphatic aldehydes by [V2Cl3(THF)6]2[Zn2Cl 6]. Synthesis of syn,syn-3-[N-(alkoxycarbonyl)amino] 1,2-diols

Slow addition of 2-[N-(alkoxycarbonyl)amino] aldehydes to mixtures of [V2Cl3(THF)6]2[Zn2Cl 6] and aliphatic aldehydes gave syn,syn-3-[N-(alkoxycarbonyl)amino] 1,2-diols in good yield and high enantiomeric purity (>99:1). The alkyl group of the N-alkoxycarbonyl was shown to influence the yield: Me > allyl > Bn > t-Bu. Only the syn,syn diastereomer was observed (>20:1), except with N-Cbz-alaninal (10:1:1), O-benzyl-N-Cbz-serinal (7:1), and N-Cbz-prolinal (5:1 to 12:1). A new serinai derivative, N-Cbz-O-TBS-serinal, was cross coupled with n-pentadecanal to give a derivative of xylo-D-C18-phytosphingosine.

Pinacol Homocoupling of (S)-2- Aldehydes by 2. Synthesis of C2-Symmetric (1S,2R,3R,4S)-1,4-Diamino 2,3-Diols

Six (S)-2- aldehydes 3a-f were homocoupled by 2 (1) to give C2-symmetric (1S,2R,3R,4S)-1,4-bis 2,3-diols 4a-f in good yield.High-yield conversions of the diols to biso

One-step transformation of α-amino acids to α-amino aldehydes effected by electrochemical oxidation of Ph3P

The electrolysis of triphenylphosphine and L-α-amino acids in one compartment cell under a nitrogen atmosphere at -30°C gave L-α-amino aldehydes in good yields with no or little racemization when triphenylphosphonium perchlorate was used as a supporting electrolyte.