(1S,3Z)-1-allyl-3-bromo-4-phenylbut-3-enyl (2S)-2-({3-[(N-acryloyl-3-chloro-O-methyl-D-tyrosyl)amino]-2,2-dimethylpropanoyl}oxy)-4-methylpentanoate

Base Information

• Chemical Name: (1S,3Z)-1-allyl-3-bromo-4-phenylbut-3-enyl (2S)-2-({3-[(N-acryloyl-3-chloro-O-methyl-D-tyrosyl)amino]-2,2-dimethylpropanoyl}oxy)-4-methylpentanoate
• CAS No.: 905309-76-4
• Molecular Formula: C₃₇H₄₆BrClN₂O₇
• Molecular Weight: 746.138
• Mol file: 905309-76-4.mol

Synonyms:(1S,3Z)-1-allyl-3-bromo-4-phenylbut-3-enyl (2S)-2-({3-[(N-acryloyl-3-chloro-O-methyl-D-tyrosyl)amino]-2,2-dimethylpropanoyl}oxy)-4-methylpentanoate

Chemical Property of (1S,3Z)-1-allyl-3-bromo-4-phenylbut-3-enyl (2S)-2-({3-[(N-acryloyl-3-chloro-O-methyl-D-tyrosyl)amino]-2,2-dimethylpropanoyl}oxy)-4-methylpentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3Z)-1-allyl-3-bromo-4-phenylbut-3-enyl (2S)-2-({3-[(N-acryloyl-3-chloro-O-methyl-D-tyrosyl)amino]-2,2-dimethylpropanoyl}oxy)-4-methylpentanoate

There total 15 articles about (1S,3Z)-1-allyl-3-bromo-4-phenylbut-3-enyl (2S)-2-({3-[(N-acryloyl-3-chloro-O-methyl-D-tyrosyl)amino]-2,2-dimethylpropanoyl}oxy)-4-methylpentanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

allyl (2S)-2-({3-[(N-acryloyl-3-chloro-O-methyl-D-tyrosyl)amino]-2,2-dimethylpropanoyl}oxy)-4-methylpentanoate (905309-67-3) + (1Z,4S)-2-bromo-1-phenylhepta-1,6-dien-4-ol (905309-65-1) → (1S,3Z)-1-allyl-3-bromo-4-phenylbut-3-enyl (2S)-2-({3-[(N-acryloyl-3-chloro-O-methyl-D-tyrosyl)amino]-2,2-dimethylpropanoyl}oxy)-4-methylpentanoate (905309-76-4)

Guidance literature:

allyl (2S)-2-({3-[(N-acryloyl-3-chloro-O-methyl-D-tyrosyl)amino]-2,2-dimethylpropanoyl}oxy)-4-methylpentanoate; With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 20 ℃; for 0.25h;

With 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 0.5h;

(1Z,4S)-2-bromo-1-phenylhepta-1,6-dien-4-ol; With dmap; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; benzene; at 20 ℃; for 16h;

DOI:10.1021/ol0609356

Reference yield:

allyl (2S)-2-[(3-amino-2,2-dimethylpropanoyl)oxy]-4-methylpentanoate (905309-55-9) → (1S,3Z)-1-allyl-3-bromo-4-phenylbut-3-enyl (2S)-2-({3-[(N-acryloyl-3-chloro-O-methyl-D-tyrosyl)amino]-2,2-dimethylpropanoyl}oxy)-4-methylpentanoate (905309-76-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 78 percent / HOBt; DIEA; EDCI / CH₂Cl₂ / 16 h / 20 °C

2.1: morpholine / Pd(PPh₃)4 / tetrahydrofuran / 0.25 h / 20 °C

2.2: DIEA; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 0.5 h / 20 °C

2.3: 85 percent / DMAP; DIEA / tetrahydrofuran; benzene / 16 h / 20 °C

With morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol0609356

Reference yield:

methyl (2R)-2-(acryloylamino)-3-(3-chloro-4-methoxyphenyl)propanoate (905309-57-1) → (1S,3Z)-1-allyl-3-bromo-4-phenylbut-3-enyl (2S)-2-({3-[(N-acryloyl-3-chloro-O-methyl-D-tyrosyl)amino]-2,2-dimethylpropanoyl}oxy)-4-methylpentanoate (905309-76-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 99 percent / LiOH / tetrahydrofuran; methanol; H₂O / 4 h / 20 °C

2.1: 78 percent / HOBt; DIEA; EDCI / CH₂Cl₂ / 16 h / 20 °C

3.1: morpholine / Pd(PPh₃)4 / tetrahydrofuran / 0.25 h / 20 °C

3.2: DIEA; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 0.5 h / 20 °C

3.3: 85 percent / DMAP; DIEA / tetrahydrofuran; benzene / 16 h / 20 °C

With morpholine; lithium hydroxide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/ol0609356

upstream raw materials:

allyl (2S)-2-({3-[(N-acryloyl-3-chloro-O-methyl-D-tyrosyl)amino]-2,2-dimethylpropanoyl}oxy)-4-methylpentanoate

(1Z,4S)-2-bromo-1-phenylhepta-1,6-dien-4-ol

allyl (2S)-2-[(3-amino-2,2-dimethylpropanoyl)oxy]-4-methylpentanoate

methyl (2R)-2-(acryloylamino)-3-(3-chloro-4-methoxyphenyl)propanoate

Downstream raw materials:

(3S,10R,16S)-16-[(2Z)-2-benzylidene-4-phenylbut-3-ynyl]-10-(3-chloro-4-methoxybenzyl)-3-isobutyl-6,6-dimethyl-1,4-dioxa-8,11-diazacyclohexadec-13-ene-2,5,9,12-tetrone

(3S,10R,16S)-16-[(2Z)-2-bromo-3-phenylprop-2-enyl]-10-(3-chloro-4-methoxybenzyl)-3-isobutyl-6,6-dimethyl-1,4-dioxa-8,11-diazacyclohexadec-13-ene-2,5,9,12-tetrone