81135-33-3

Upstream product

• 81135-32-2 (4S,5R,1'R,3'E)-2,2,3-trimethyl-5-(1'-methyl-3'-pentenyl)-4-(oxazolidinylcarbonyl)-L-2-aminobutyrylsarcosyl-N-methylleucylvalyl-N-methylleucylalanine benzyl ester 
• 81135-30-0 L-2-aminobutyryl-sarcosyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl-L-alanine benzyl ester 
• 1356155-99-1 Boc-MeLeu-SH 
• 869795-62-0 H-MeLeu-Ala-OBn hydrochloride 
• 1356203-91-2 C₃₆H₆₀N₆O₇*ClH 
• 81135-58-2 Boc-(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)-6-octensaeure 
• 81135-26-4 N-(tert-butoxycarbonyl)-L-valyl-N-methyl-L-leucyl-L-alanine benzyl ester 
• 5557-81-3 (R)-benzyl 2-aminopropanoate hydrochloride 
• 81135-31-1 (4S,5R,1'R,3'E)-2,2,3-trimethyl-5-(1'-methyl-3'-pentenyl)-4-oxazolidinecarboxylic acid 
• 59865-23-5 (2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid 
• 125714-56-9 N-(4-methoxybenzyloxycarbonyl)valyl-N-methylleucylalanine benzyl ester 
• 125714-53-6 N-<(9-fluorenylmethyl)oxy>carbonyl-N-methylleucylalanine benzyl ester 
• 81135-28-6 N-methylleucylvalyl-N-methylleucylalanine benzyl ester 
• 125714-55-8 N-(2-trimethylsilylethyloxycarbonyl)valyl-N-methylleucylalanine benzyl ester 

Downstream Products

• 104186-79-0 N^α-<(9-fluorenylmethyl)oxy>carbonyl-N^ε-(tert-butyloxycarbonyl)-D-lysyl-N-methylleucyl-N-methylleucyl-N-methylvalyl-(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)-6-octenoyl-L-2-aminobutyrylsarcosyl-N-methylleucylvalyl-N-methylleucylalanyl ben... 

Relevant academic research and scientific papers

Expanding the limits of isonitrile-mediated amidations: On the remarkable stereosubtleties of macrolactam formation from synthetic seco -cyclosporins

The scope of isonitrile-mediated amide bond-forming reactions is further explored in this second-generation synthetic approach to cyclosporine (cyclosporin A). Both type I and type II amidations are utilized in this effort, allowing access to epimeric cyclosporins A and H from a single precursor by variation of the coupling reagents. This work lends deeper insight into the relative acylating ability of the formimidate carboxylate mixed anhydride (FCMA) intermediate, while shedding light on the far-reaching impact of remote stereochemical changes on the effective preorganization of seco-cyclosporins.

Total synthesis of cyclosporine: Access to N-methylated peptides via lsonitrile coupling reactions

Recent developments in the use of isonitriles to furnish secondary and tertiary amide bond formations have been applied to a novel total synthesis of the important cyclic polypeptide cyclosporine A. Specifically, the disclosed synthetic route demonstrates the utility of microwave-mediated carboxylic acid isonitrile couplings, thioacid isonitrile couplings at ambient temperature, and isonitrile-mediated couplings of carboxylic acids and thioacids with amines to form challenging amide bonds. Copyright

Synthesis of D-lysine8-cyclosporine A. Further characterization of BOP-C1 in the 2-7 hexapeptide fragment synthesis

The coupling reagent N,N-bis(2-oxo-3-oxazolidinyl)phosphinic chloride (BOP-Cl) has been used to synthesize the 2-7 hexapeptide fragment of cyclosporine A. The reagent proved useful in four of the five coupling steps with yields ranging from 78 to 92%. Ove