3339-45-5

Upstream product

• 67-56-1 methanol 
• 202273-47-0 (S)-4-Isobutyl-3-methyl-2,2-bis-trifluoromethyl-oxazolidin-5-one 
• 61-90-5 L-leucine 
• 6458-39-5 (S)-4-isobutyl-2,2-bis-trifluoromethyl-oxazolidin-5-one 
• 202273-39-0 (S)-3-Chloromethyl-4-isobutyl-2,2-bis-trifluoromethyl-oxazolidin-5-one 
• 3060-46-6 N-methyl-L-leucine 
• 130994-88-6 methyl N-methyl-N-(tert-butoxycarbonyl)-L-leucinate 

Downstream Products

• 3339-41-1 O-Benzyloxycarbonyl-D-α-hydroxy-isovaleryl-N-methyl-L-leucin-O-methylester 
• 1242265-12-8 (3S,6S)-3-benzyl-6-isobutyl-1,4-dimethylpiperazine-2,5-dione 
• 1357008-65-1 methyl (S)-2-[(S)-2-(tert-butoxycarbonylamino)-N-methyl-3-phenylpropanamido]-4-methylpentanoate 

Relevant academic research and scientific papers

Synthesis and stereochemistry of JBIR-81, a peptide enamide derived from aspergilli

The absolute stereochemistry of an aspergilli-derived peptide enamide, JBIR-81, was determined to be 12S, 15S by the first synthesis of (12S,15S)-JBIR-81 and its epimer. The overall yield was 56% over six steps from N-methyl-L-leucine. The (Z)-enamide structure was effectively constructed with use of a copper (I) catalyzed coupling reaction between a vinyl halide and a carboxamide.

Synthetic studies towards Pseudoxylallemycin B, an antibiotic active against gram-negative bacteria: Total synthesis of 3-epi-Pseudoxylallemycin B

In an attempt towards the total synthesis of Pseudoxylallemycin B, a homo dimeric, N-methylated macrocyclic tetrapeptidic natural product, synthesis of its epimer at position 3 (D-Tyr instead of L-Tyr) is described here. During the course of synthesis we came across a striking yet unusual observation of complete epimerization which led to the formation of 3-epi-Pseudoxylallemycin B.

An efficient synthesis of N-methylamino acids and some of their derivatives

N-Methylamino acid derivatives are obtained in high yield by a stereoselective one-pot procedure from hexafluoroacetone protected amino acids via N-chloromethylation and treatment with triethylsilane/trifluoroacetic acid.