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149606-27-9

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Basic Information
CAS No.: 149606-27-9
Name: (2S)-2-[[(2S)-2-dimethylamino-3-methyl-butanoyl]amino]-N-[(3R,4S,5S)-3 -methoxy-1-[(3R)-3-[(1R,2R)-1-methoxy-2-(phenethylcarbamoyl)propyl]pyr rolidin-1-yl]-5-methyl-1-oxo-heptan-4-yl]-N,3-dimethyl-butanamide
Article Data: 2
Molecular Structure:
Molecular Structure of 149606-27-9 ((2S)-2-[[(2S)-2-dimethylamino-3-methyl-butanoyl]amino]-N-[(3R,4S,5S)-3 -methoxy-1-[(3R)-3-[(1R,2R)-1-methoxy-2-(phenethylcarbamoyl)propyl]pyr rolidin-1-yl]-5-methyl-1-oxo-heptan-4-yl]-N,3-dimethyl-butanamide)
Formula: C39H67 N5 O6
Molecular Weight: 701.991
Synonyms: L-Valinamide,N,N-dimethyl-L-valyl-N-[2-methoxy-4-[2-[1-methoxy-2-methyl-3-oxo-3-[(2-phenylethyl)amino]propyl]-1-pyrrolidinyl]-1-(1-methylpropyl)-4-oxobutyl]-N-methyl-,[2S-[1[1R*(R*),2S*],2R*(1S*,2S*)]]-; Auristatin PE; Soblidotin; TZT 1027
Density: 1.064g/cm3
Melting Point: 73-79 °C
Boiling Point: 843.4°Cat760mmHg
Flash Point: 463.9°C
PSA: 120.52000
LogP: 4.71230
Related products
Synthetic route
64-04-0

phenethylamine

163768-53-4

Dov-Val-Dil-Dap

149606-27-9

TZT-1027

Conditions
ConditionsYield
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide Yield given;
With triethylamine; diethyl cyano phosphate In DMF (N,N-dimethyl-formamide)
135383-56-1

(3R,4S,5S)-4--3-methoxy-5-methylheptanoic acid

149606-27-9

TZT-1027

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: H2SO4 / CH2Cl2
2: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h
3: 1,3-dicyclohexylcarbodiimide / CH2Cl2
4: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h
5: diethyl phosphorocyanidate, Et3N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h
6: trifluoroacetic acid / CH2Cl2 / 1 h / Ambient temperature
7: diethyl phosphorocyanidate, Et3N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h
8: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h
9: diethyl phosphorocyanidate, Et3N / dimethylformamide
View Scheme
120205-58-5

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

149606-27-9

TZT-1027

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h
2: 1,3-dicyclohexylcarbodiimide / CH2Cl2
3: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h
4: diethyl phosphorocyanidate, Et3N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h
5: trifluoroacetic acid / CH2Cl2 / 1 h / Ambient temperature
6: diethyl phosphorocyanidate, Et3N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h
7: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h
8: diethyl phosphorocyanidate, Et3N / dimethylformamide
View Scheme
474645-22-2

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

149606-27-9

TZT-1027

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 1,3-dicyclohexylcarbodiimide / CH2Cl2
2: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h
3: diethyl phosphorocyanidate, Et3N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h
4: trifluoroacetic acid / CH2Cl2 / 1 h / Ambient temperature
5: diethyl phosphorocyanidate, Et3N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h
6: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h
7: diethyl phosphorocyanidate, Et3N / dimethylformamide
View Scheme
120205-53-0

(3R,4S,5S)-tert-butyl 4-((S)-2-((S)-2-(dimethylamino)-3-methylbutanamido)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoate

149606-27-9

TZT-1027

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: trifluoroacetic acid / CH2Cl2 / 1 h / Ambient temperature
2: diethyl phosphorocyanidate, Et3N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h
3: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h
4: diethyl phosphorocyanidate, Et3N / dimethylformamide
View Scheme
120205-52-9

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

149606-27-9

TZT-1027

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h
2: diethyl phosphorocyanidate, Et3N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h
3: trifluoroacetic acid / CH2Cl2 / 1 h / Ambient temperature
4: diethyl phosphorocyanidate, Et3N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h
5: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h
6: diethyl phosphorocyanidate, Et3N / dimethylformamide
View Scheme
163768-52-3

Dov-Val-Dil-Dap-OBzl

149606-27-9

TZT-1027

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h
2: diethyl phosphorocyanidate, Et3N / dimethylformamide
View Scheme
177423-00-6

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

149606-27-9

TZT-1027

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: diethyl phosphorocyanidate, Et3N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h
2: trifluoroacetic acid / CH2Cl2 / 1 h / Ambient temperature
3: diethyl phosphorocyanidate, Et3N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h
4: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h
5: diethyl phosphorocyanidate, Et3N / dimethylformamide
View Scheme
149664-79-9

(3R,4S,5S)-4-(Benzyloxycarbonyl-methyl-amino)-3-methoxy-5-methyl-heptanoic acid methyl ester

149606-27-9

TZT-1027

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 1N aq. NaOH / dioxane / 3 h / Ambient temperature
2: H2SO4 / CH2Cl2
3: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h
4: 1,3-dicyclohexylcarbodiimide / CH2Cl2
5: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h
6: diethyl phosphorocyanidate, Et3N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h
7: trifluoroacetic acid / CH2Cl2 / 1 h / Ambient temperature
8: diethyl phosphorocyanidate, Et3N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h
9: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h
10: diethyl phosphorocyanidate, Et3N / dimethylformamide
View Scheme
133120-89-5

(3R,4S,5S)-4-((S)-2-((S)-2-(dimethylamino)-3-methylbutanamido)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoic acid

149606-27-9

TZT-1027

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: diethyl phosphorocyanidate, Et3N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h
2: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h
3: diethyl phosphorocyanidate, Et3N / dimethylformamide
View Scheme
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