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CAS 121584-52-9

Cyclo[[3(R)-acetoxy-N2,4(R)-dimethyl-6-oxo-L-norleucyl]-L-2-aminobutyryl-N-methyl-G-N-methyl-LV-N-methyl-LAa-N-methyl-L-N-methyl-L-N-methyl-V]

Codes: Voclosporin-004

Application context (from source-drug indications)

狼疮肾炎VoclosporinKidney transplant rejectionVoclosporinCOVID-19VoclosporinSystemic lupus erythematosusVoclosporin局灶性节段性肾小球硬化症VoclosporinDry eye syndromeVoclosporin

Source drugs (routes using this intermediate)

DrugTierExpiry
VoclosporinTier C — Watch / trade-

Position in synthesis routes (up/downstream chain)

Ordered by route registration; left → right is the synthesis direction. The highlighted node is the current CAS; others link to their own profiles.

VoclosporinOptimised routesteps: 2total yield: /
Cyclo{-[4-( E)-but-2-enyl- N,4-dimethyl- L-threonyl]-L-homoalanyl-(N-methylglycyl)-( N-methyl-L-leucyl)-L-valyl-( N-me-thyl- L-leucyl)-L-alanyl- D-alanyl-(N-methyl-L-leucyl)-( N-methyl-L-leucyl)-(N-methyl-L-valyl)-}→(1R,2R,4E)-1-[(2S,5S,11S,14S,17S,20S,23R,26S,29S,32S)-5-Ethyl-1,7,10,16,20,23,25,28,31-nonamethyl-11,17,26,29-tetrakis(2-methylpropyl)-3,6,9,12,15,18,21,24,27,30,33-undecaoxo-14,32-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontan-2-yl]-2-methylhex-4-en-1-ylacetate→(1R,2R,4E)-1-[(2S,5S,11S,14S,17S,20S,23R,26S,29S,32S)-5-Ethyl-1,7,10,16,20,23,25,28,31-nonamethyl-11,17,26,29-tetrakis(2-methylpropyl)-3,6,9,12,15,18,21,24,27,30,33-undecaoxo-14,32-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontan-2-yl]-2-methylhex-4-en-1-ylbenzoate→Cyclo[[3(R)-acetoxy-N2,4(R)-dimethyl-6-oxo-L-norleucyl]-L-2-aminobutyryl-N-methyl-G-N-methyl-LV-N-methyl-LAa-N-methyl-L-N-methyl-L-N-methyl-V]→(1R,2R)-1-[(2S,5S,11S,14S,17S,20S,23R,26S,29S,32S)-5-Ethyl-1,7,10,16,20,23,25,28,31-nonamethyl-11,17,26,29-tetrakis(2-methylpropyl)-3,6,9,12,15,18,21,24,27,30,33-undecaoxo-14,32-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontan-2-yl]-2-methyl-4-oxobutylbenzoate
VoclosporinOptimised routesteps: 2total yield: 9.6g(Voclosporin (Free))
Cyclo[[3(R)-acetoxy-N2,4(R)-dimethyl-6-oxo-L-norleucyl]-L-2-aminobutyryl-N-methyl-G-N-methyl-LV-N-methyl-LAa-N-methyl-L-N-methyl-L-N-methyl-V]→(1R,2R)-1-[(2S,5S,11S,14S,17S,20S,23R,26S,29S,32S)-5-Ethyl-1,7,10,16,20,23,25,28,31-nonamethyl-11,17,26,29-tetrakis(2-methylpropyl)-3,6,9,12,15,18,21,24,27,30,33-undecaoxo-14,32-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontan-2-yl]-2-methyl-4-oxobutylbenzoate→Triphenyl(prop-2-en-1-yl)phosphoniumbromide→(1R,2R,4E)-1-[(2S,5S,11S,14S,17S,20S,23R,26S,29S,32S)-5-Ethyl-1,7,10,16,20,23,25,28,31-nonamethyl-11,17,26,29-tetrakis(2-methylpropyl)-3,6,9,12,15,18,21,24,27,30,33-undecaoxo-14,32-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontan-2-yl]-2-methylhepta-4,6-dien-1-ylacetate→(1R,2R,4E)-1-[(2S,5S,11S,14S,17S,20S,23R,26S,29S,32S)-5-Ethyl-1,7,10,16,20,23,25,28,31-nonamethyl-11,17,26,29-tetrakis(2-methylpropyl)-3,6,9,12,15,18,21,24,27,30,33-undecaoxo-14,32-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontan-2-yl]-2-methylhepta-4,6-dien-1-ylbenzoate→[Phenyl(prop-2-en-1-yl)phosphoroso]benzene→Dimethylallylphosphonate
VoclosporinOptimised routesteps: 2total yield: 14.09g(Voclosporin (Free))
Cyclo[[3(R)-acetoxy-N2,4(R)-dimethyl-6-oxo-L-norleucyl]-L-2-aminobutyryl-N-methyl-G-N-methyl-LV-N-methyl-LAa-N-methyl-L-N-methyl-L-N-methyl-V]→trimethyl[(1E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-1-en-1-yl]silane→(1R,2R,4R,5R)-1-[(2S,5S,11S,14S,17S,20S,23R,26S,29S,32S)-5-ethyl-14,32-diisopropyl-1,7,10,16,20,23,25,28,31-nonamethyl-11,17,26,29-tetrakis(2-methylpropyl)-3,6,9,12,15,18,21,24,27,30,33-undecaoxo-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontan-2-yl]-4-hydroxy-2-methyl-5-(trimethylsilyl)hept-6-en-1-ylacetate
VoclosporinOptimised routesteps: 2total yield: 4.92g(Voclosporin-004)
Cyclo{-[4-( E)-but-2-enyl- N,4-dimethyl- L-threonyl]-L-homoalanyl-(N-methylglycyl)-( N-methyl-L-leucyl)-L-valyl-( N-me-thyl- L-leucyl)-L-alanyl- D-alanyl-(N-methyl-L-leucyl)-( N-methyl-L-leucyl)-(N-methyl-L-valyl)-}→(1R,2R,4E)-1-[(2S,5S,11S,14S,17S,20S,23R,26S,29S,32S)-5-Ethyl-1,7,10,16,20,23,25,28,31-nonamethyl-11,17,26,29-tetrakis(2-methylpropyl)-3,6,9,12,15,18,21,24,27,30,33-undecaoxo-14,32-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontan-2-yl]-2-methylhex-4-en-1-ylacetate→Cyclo[[3(R)-acetoxy-N2,4(R)-dimethyl-6-oxo-L-norleucyl]-L-2-aminobutyryl-N-methyl-G-N-methyl-LV-N-methyl-LAa-N-methyl-L-N-methyl-L-N-methyl-V]

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