93299-38-8

Upstream product

• 93272-06-1 5-bromo-N_b-methoxycarbonyl-D-tryptophan methyl ester 
• 139393-00-3 8-Acetyl-5-bromo-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid dimethyl ester 
• 67811-39-6 8-Acetyl-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid dimethyl ester 
• 93272-06-1 5-bromo-N_b-methoxycarbonyl-L-tryptophan methyl ester 
• 83541-81-5 (S)-dimethyl pyrrolidine-1,2-dicarboxylate 
• 93271-98-8 N-methoxycarbonyl-4-cyano-L-2-aminobutyric acid methyl ester 
• 93271-96-6 (2S,5RS)-1,2-dimethyl-5-hydroxypyrrolidine-1,2-dicarboxylate 
• 93299-30-0 N-methoxycarbonyl-L-glutamine methyl ester 
• 147-85-3 L-proline 
• 74761-41-4 (S)-1-(methoxycarbonyl)pyrrolidine-2-carboxylic acid 
• 67-56-1 methanol 
• 6548-09-0 5-bromo-DL-tryptophan 
• 1370458-21-1 dimethyl (2S,3aR,8aS)-8-acetyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-1,2-dicarboxylate 
• 1370458-22-2 dimethyl (2S,3aR,8aS)-8-acetyl-5-bromo-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-1,2-dicarboxylate 

Downstream Products

• 1370458-23-3 Boc-Ise(TBDPS)-Trp(5-Br)-OMe 
• 1370458-05-1 Boc-Ise(TBDPS)-Trp(5-Br)-OH 
• 1370458-06-2 C₅₆H₆₅BrCl₄N₈O₁₃Si 
• 1370458-07-3 C₄₀H₄₇BrCl₄N₈O₁₃ 
• 1370458-17-5 C₄₇H₄₇BrCl₄N₈O₁₀Si 
• 1370458-18-6 C₄₀H₄₇BrCl₄N₈O₁₃ 
• 1370458-08-4 C₅₆H₆₅BrCl₄N₈O₁₃Si 
• 1370458-09-5 C₄₇H₄₇BrCl₄N₈O₁₀Si 
• 6548-09-0 5-bromo-L-tryptophan 

Relevant academic research and scientific papers

A One-Pot Synthesis of Symmetrical and Unsymmetrical Dipeptide Ureas

We describe a flexible and high yielding synthesis of 1,3-disubstituted ureas that allows for the construction of both symmetrical and unsymmetrical dipeptide ureas, including easy access to 13C-labelled ureas, from amino acids and carbon dioxide at atmospheric pressure. We describe a flexible and high yielding synthesis of 1,3-disubstituted ureas, that allows for the construction of both symmetrical and unsymmetrical dipeptide ureas, including easy access to 13C labelled ureas, from amino acids and carbon dioxide at atmospheric pressure.

Total synthesis of nominal (11S)- and (11R)-cyclocinamide A

The cyclocinamides possess a unique β2αβ 2α 14-membered tetrapeptide core. The initially reported biological data and intriguing structure, which was without full stereochemical identification, necessitated synthesis of both nominal (all-S) cyclocinamide A and the 11R isomer. The completed synthesis is highlighted by the use of a (cyclo)asparagine-containing dipeptide as a turn inducing fragment. Due to inconsistencies in analytical data between natural and synthetic samples, a re-evaluation of the natural product stereochemistry appears necessary.

N-benzoyl amino acids as LFA-1/ICAM inhibitors 1: Amino acid structure-activity relationship

The association of ICAM-1 with LFA-1 plays a critical role in several autoimmune diseases. N-2-Bromobenzoyl L-tryptophan, compound 1, was identified as an inhibitor to the formation of the LFA-1/ICAM complex. The SAR of the amino acid indicates that the carboxylic acid is required for inhibition and that L-histidine is the most favored amino acid.

Syntheses of Substituted L- and D-Tryptophans

Several 5-substituted nb-methoxycarbonyl-L- and -D-tryptophan derivatives were synthesized from proline by a new route involving electrochemical oxidation, as well as by the known procedures.Removal of the Nb-methoxycarbonyl group was accomplished by treatment with Me3SiI in refluxing chloroform, then alkaline hydrolysis of the methyl esters afforded 5-substituted L- and D-tryptophans with high optical purities.Keywords - L-tryptophan 5-substituted; D-tryptophan 5-substituted; anodic oxidation; N-methoxycarbonyl group deprotection; Fischer indole synthesis; iodotrimethylsilane