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

Base Information

• Chemical Name: (3S,10R,16R)-10-(3-chloro-4-methoxybenzyl)-16-[(2Z)-3-iodo-3-phenylprop-2-enyl]-3-isobutyl-6,6-dimethyl-1,4-dioxa-8,11-diazacyclohexadec-13-ene-2,5,9,12-tetrone
• CAS No.: 905309-81-1
• Molecular Formula: C₃₅H₄₂ClIN₂O₇
• Molecular Weight: 765.085
• Mol file: 905309-81-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 19 articles about (3S,10R,16R)-10-(3-chloro-4-methoxybenzyl)-16-[(2Z)-3-iodo-3-phenylprop-2-enyl]-3-isobutyl-6,6-dimethyl-1,4-dioxa-8,11-diazacyclohexadec-13-ene-2,5,9,12-tetrone 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: 84.0%

(1R,3Z)-1-allyl-4-iodo-4-phenylbut-3-enyl (2S)-2-({3-[(N-acryloyl-3-chloro-O-methyl-D-tyrosyl)amino]-2,2-dimethylpropanoyl}oxy)-4-methylpentanoate (905309-82-2) → (3S,10R,16R)-10-(3-chloro-4-methoxybenzyl)-16-[(2Z)-3-iodo-3-phenylprop-2-enyl]-3-isobutyl-6,6-dimethyl-1,4-dioxa-8,11-diazacyclohexadec-13-ene-2,5,9,12-tetrone (905309-81-1)

Guidance literature:

Grubbs catalyst first generation; In toluene; at 80 ℃; for 48h;

DOI:10.1021/ol0609356

Reference yield: 24.0%

(1R,3Z)-1-allyl-4-iodo-4-phenylbut-3-enyl (2S)-2-({3-[(N-acryloyl-3-chloro-O-methyl-D-tyrosyl)amino]-2,2-dimethylpropanoyl}oxy)-4-methylpentanoate (905309-82-2) → (3S,10R,16S)-16-allyl-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,16R)-10-(3-chloro-4-methoxybenzyl)-16-[(2Z)-3-iodo-3-phenylprop-2-enyl]-3-isobutyl-6,6-dimethyl-1,4-dioxa-8,11-diazacyclohexadec-13-ene-2,5,9,12-tetrone (905309-81-1)

Guidance literature:

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; for 40h; Heating;

DOI:10.1021/ol0609356

Reference yield:

(1Z,4R)-1-iodo-1-phenylhepta-1,6-dien-4-ol (905451-66-3) → (3S,10R,16R)-10-(3-chloro-4-methoxybenzyl)-16-[(2Z)-3-iodo-3-phenylprop-2-enyl]-3-isobutyl-6,6-dimethyl-1,4-dioxa-8,11-diazacyclohexadec-13-ene-2,5,9,12-tetrone (905309-81-1)

Guidance literature:

Multi-step reaction with 2 steps

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

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

1.3: 72 percent / DMAP; DIEA / tetrahydrofuran; benzene / 16 h / 20 °C

2.1: 31 percent / (1,3-dimesitylimidazolidin-2-ylidene)RuCl₂(PCy₃)(=CHPh) / CH₂Cl₂ / 40 h / Heating

With morpholine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol0609356

upstream raw materials:

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

(1Z,4R)-1-iodo-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