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863971-44-2

Basic Information
CAS No.: 863971-44-2
Name: (5S,9S,11S,12R)-11-((S)-sec-butyl)-1-(9H-fluoren-9-yl)-5,9-diisopropyl-12-Methoxy-4,10-diMethyl-3,6,8-trioxo-2-oxa-4,7,10-triazatetradecan-14-oic acid
Article Data: 6
Molecular Structure:
Molecular Structure of 863971-44-2 ((5S,9S,11S,12R)-11-((S)-sec-butyl)-1-(9H-fluoren-9-yl)-5,9-diisopropyl-12-Methoxy-4,10-diMethyl-3,6,8-trioxo-2-oxa-4,7,10-triazatetradecan-14-oic acid)
Formula: C36H51N3O7
Molecular Weight: 637.817
Synonyms: (5S,9S,11S,12R)-11-((S)-sec-butyl)-1-(9H-fluoren-9-yl)-5,9-diisopropyl-12-Methoxy-4,10-diMethyl-3,6,8-trioxo-2-oxa-4,7,10-triazatetradecan-14-oic acid;Fmoc-3AA-orl;Fmoc-3vvd-OH;Tripeptide (MMAE-3)
PSA: 125.48000
LogP: 5.78640
Synthetic route
474645-25-5

tert-butyl (5S,8S,11S,12R)-11-((S)-sec-butyl)-1-(9H-fluoren-9-yl)-5,8-diisopropyl-12-methoxy-4,10-dimethyl-3,6,9-trioxo-2-oxa-4,7,10-triazatetradecan-14-oate

863971-44-2

(5S,8S,11S,12R)-11-((S)-sec-butyl)-1-(9H fluoren-9-yl)-5,8-diisopropyl-12-methoxy-4,10-dimethyl-3,6,9-trioxo-2-oxa-4,7,10-triazatetradecan-14-oic acid

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃; for 2h;86%
With trifluoroacetic acid In dichloromethane
With trifluoroacetic acid In dichloromethane
177423-00-6

(3R,4S,5S)-4-[(2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-N,3-dimethylbutanamido]-3-methoxy-5-methylheptanoate

863971-44-2

(5S,8S,11S,12R)-11-((S)-sec-butyl)-1-(9H fluoren-9-yl)-5,8-diisopropyl-12-methoxy-4,10-dimethyl-3,6,9-trioxo-2-oxa-4,7,10-triazatetradecan-14-oic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C
2: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C
2: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine; diethyl dicarbonate / ethyl acetate / 20 °C
2: trifluoroacetic acid / dichloromethane / 20 °C
View Scheme
474645-22-2

tert-Butyl (3R,4S,5S)-3-methoxy-4-(N-methylamino)-5-methylheptanoate

863971-44-2

(5S,8S,11S,12R)-11-((S)-sec-butyl)-1-(9H fluoren-9-yl)-5,8-diisopropyl-12-methoxy-4,10-dimethyl-3,6,9-trioxo-2-oxa-4,7,10-triazatetradecan-14-oic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 2-bromo-1-ethylpyridin-1-ium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 h / -10 - 20 °C
2: palladium 10% on activated carbon; hydrogen / methanol / 1 h / 20 °C
3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C
4: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: N-ethyl-N,N-diisopropylamine; 2-bromo-1-ethylpyridinium tetrafluoroborate / dichloromethane / 20 h / -10 - 20 °C
2: palladium 10% on activated carbon; hydrogen / methanol / 1 h / 20 °C
3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C
4: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
View Scheme
1149-26-4

(S)-N-(benzyloxycarbonyl)valine

863971-44-2

(5S,8S,11S,12R)-11-((S)-sec-butyl)-1-(9H fluoren-9-yl)-5,8-diisopropyl-12-methoxy-4,10-dimethyl-3,6,9-trioxo-2-oxa-4,7,10-triazatetradecan-14-oic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 2-bromo-1-ethylpyridin-1-ium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 h / -10 - 20 °C
2: palladium 10% on activated carbon; hydrogen / methanol / 1 h / 20 °C
3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C
4: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: N-ethyl-N,N-diisopropylamine; 2-bromo-1-ethylpyridinium tetrafluoroborate / dichloromethane / 20 h / -10 - 20 °C
2: palladium 10% on activated carbon; hydrogen / methanol / 1 h / 20 °C
3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C
4: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
View Scheme
120205-52-9

tert-butyl (3R,4S,5S)-4-[(2S)-2-[[(benzyloxy)carbonyl]amino]-N,3-dimethylbutanamido]-3-methoxy-5-methylheptanoate

863971-44-2

(5S,8S,11S,12R)-11-((S)-sec-butyl)-1-(9H fluoren-9-yl)-5,8-diisopropyl-12-methoxy-4,10-dimethyl-3,6,9-trioxo-2-oxa-4,7,10-triazatetradecan-14-oic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: palladium 10% on activated carbon; hydrogen / methanol / 1 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C
3: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: palladium 10% on activated carbon; hydrogen / methanol / 1 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C
3: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
View Scheme
68858-20-8

Fmoc-Val-OH

863971-44-2

(5S,8S,11S,12R)-11-((S)-sec-butyl)-1-(9H fluoren-9-yl)-5,8-diisopropyl-12-methoxy-4,10-dimethyl-3,6,9-trioxo-2-oxa-4,7,10-triazatetradecan-14-oic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 2-chloro-4,6-dimethoxy-1 ,3,5-triazine / 20 °C
2: diethylamine / tetrahydrofuran / 20 °C
3: N-ethyl-N,N-diisopropylamine; diethyl dicarbonate / ethyl acetate / 20 °C
4: trifluoroacetic acid / dichloromethane / 20 °C
View Scheme
1375415-93-2

tert-butyl (3R,4S,5S)-4-[(2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-N,3-dimethylbutanamido]-3-methoxy-5-methylheptanoate

863971-44-2

(5S,8S,11S,12R)-11-((S)-sec-butyl)-1-(9H fluoren-9-yl)-5,8-diisopropyl-12-methoxy-4,10-dimethyl-3,6,9-trioxo-2-oxa-4,7,10-triazatetradecan-14-oic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: diethylamine / tetrahydrofuran / 20 °C
2: N-ethyl-N,N-diisopropylamine; diethyl dicarbonate / ethyl acetate / 20 °C
3: trifluoroacetic acid / dichloromethane / 20 °C
View Scheme
120205-48-3

tert-Butyl (3R,4S,5S)-3-methoxy-4-(N-methylamino)-5-methylheptanoate hydrochloride

863971-44-2

(5S,8S,11S,12R)-11-((S)-sec-butyl)-1-(9H fluoren-9-yl)-5,8-diisopropyl-12-methoxy-4,10-dimethyl-3,6,9-trioxo-2-oxa-4,7,10-triazatetradecan-14-oic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 2-chloro-4,6-dimethoxy-1 ,3,5-triazine / 20 °C
2: diethylamine / tetrahydrofuran / 20 °C
3: N-ethyl-N,N-diisopropylamine; diethyl dicarbonate / ethyl acetate / 20 °C
4: trifluoroacetic acid / dichloromethane / 20 °C
View Scheme
863971-44-2

(5S,8S,11S,12R)-11-((S)-sec-butyl)-1-(9H fluoren-9-yl)-5,8-diisopropyl-12-methoxy-4,10-dimethyl-3,6,9-trioxo-2-oxa-4,7,10-triazatetradecan-14-oic acid

1352201-70-7

(2R,3R)-3-methoxy-2-methyl-N-[(2S)-1-(1,2-oxazinan-2-yl)-1-oxo-3-phenylpropan-2-yl]-3-[(2S)-pyrrolidin-2-yl]propanamide, trifluoroacetic acid salt

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-methyl-L-valyl-N-[(3R,4S,5S)-3-methoxy-1-{(2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-{[(2S)-1-(1,2-oxazinan-2-yl)-1-oxo-3-phenylpropan-2-yl]amino}-3-oxopropyl]pyrrolidin-1-yl}-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 3h;100%
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 3h;100%
863971-44-2

(5S,8S,11S,12R)-11-((S)-sec-butyl)-1-(9H fluoren-9-yl)-5,8-diisopropyl-12-methoxy-4,10-dimethyl-3,6,9-trioxo-2-oxa-4,7,10-triazatetradecan-14-oic acid

1352201-95-6

(2R,3R)-3-methoxy-2-methyl-N-[(2S,3S)-1-(1,2-oxazinan-2-yl)-1-oxo-3-phenylbutan-2-yl]-3-[(2S)-pyrrolidin-2-yl]propanamide, trifluoroacetic acid salt

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-methyl-L-valyl-N-[(3R,4S,5S)-3-methoxy-1-{(2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-{[(2S,3S)-1-(1,2-oxazinan-2-yl)-1-oxo-3-phenylbutan-2-yl]amino}-3-oxopropyl]pyrrolidin-1-yl}-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;100%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;100%
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