(E)-(5S,11S,14S,17R,18R)-11-[3-(tert-butyldimethylsilanyloxy)benzyl]-14-isopropyl-18-methoxy-17-methyl-3-oxa-9,12,15,28-tetraazatricyclo[21.3.1.1^5,9]octacosa-1⁽²⁷⁾,21,23,25-tetraene-4,10,13,16-tetraone

Base Information

• Chemical Name: (E)-(5S,11S,14S,17R,18R)-11-[3-(tert-butyldimethylsilanyloxy)benzyl]-14-isopropyl-18-methoxy-17-methyl-3-oxa-9,12,15,28-tetraazatricyclo[21.3.1.1^5,9]octacosa-1⁽²⁷⁾,21,23,25-tetraene-4,10,13,16-tetraone
• CAS No.: 1381816-56-3
• Molecular Formula: C₄₁H₆₀N₄O₇Si
• Molecular Weight: 749.035

Synonyms:(E)-(5S,11S,14S,17R,18R)-11-[3-(tert-butyldimethylsilanyloxy)benzyl]-14-isopropyl-18-methoxy-17-methyl-3-oxa-9,12,15,28-tetraazatricyclo[21.3.1.1^5,9]octacosa-1⁽²⁷⁾,21,23,25-tetraene-4,10,13,16-tetraone

Chemical Property of (E)-(5S,11S,14S,17R,18R)-11-[3-(tert-butyldimethylsilanyloxy)benzyl]-14-isopropyl-18-methoxy-17-methyl-3-oxa-9,12,15,28-tetraazatricyclo[21.3.1.1^5,9]octacosa-1⁽²⁷⁾,21,23,25-tetraene-4,10,13,16-tetraone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(5S,11S,14S,17R,18R)-11-[3-(tert-butyldimethylsilanyloxy)benzyl]-14-isopropyl-18-methoxy-17-methyl-3-oxa-9,12,15,28-tetraazatricyclo[21.3.1.1^5,9]octacosa-1⁽²⁷⁾,21,23,25-tetraene-4,10,13,16-tetraone

There total 11 articles about (E)-(5S,11S,14S,17R,18R)-11-[3-(tert-butyldimethylsilanyloxy)benzyl]-14-isopropyl-18-methoxy-17-methyl-3-oxa-9,12,15,28-tetraazatricyclo[21.3.1.1^5,9]octacosa-1⁽²⁷⁾,21,23,25-tetraene-4,10,13,16-tetraone 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: 75.0%

(S)-1-{(S)-3-[3-(tert-butyldimethylsilanyloxy)phenyl]-2-[(S)-2-((2R,3R)-3-methoxy-2-methylhept-6-enoylamino)-3-methylbutyrylamino]propionyl}hexahydropyridazine-3-carboxylic acid 3-vinylbenzyl ester (1381812-25-4) → (E)-(5S,11S,14S,17R,18R)-11-[3-(tert-butyldimethylsilanyloxy)benzyl]-14-isopropyl-18-methoxy-17-methyl-3-oxa-9,12,15,28-tetraazatricyclo[21.3.1.15,9]octacosa-1(27),21,23,25-tetraene-4,10,13,16-tetraone (1381816-56-3)

Guidance literature:

With Grubbs catalyst first generation; In dichloromethane; for 16h; Reflux;

DOI:10.1021/acs.jmedchem.6b01329

Reference yield:

3-Ethenylbenzyl alcohol (45804-94-2) → (E)-(5S,11S,14S,17R,18R)-11-[3-(tert-butyldimethylsilanyloxy)benzyl]-14-isopropyl-18-methoxy-17-methyl-3-oxa-9,12,15,28-tetraazatricyclo[21.3.1.15,9]octacosa-1(27),21,23,25-tetraene-4,10,13,16-tetraone (1381816-56-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / tetrahydrofuran / 6 h / 20 - 40 °C / Inert atmosphere

2.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1.5 h / 20 °C

3.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

3.2: 16 h / 0 - 20 °C / Inert atmosphere

4.1: Grubbs catalyst first generation / dichloromethane / 16 h / Reflux

With trimethylsilyl trifluoromethanesulfonate; sodium hydride; N-ethyl-N,N-diisopropylamine; HATU; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

(2R,3R)-3-methoxy-2-methyl-hept-6-enoic acid (1381812-18-5) → (E)-(5S,11S,14S,17R,18R)-11-[3-(tert-butyldimethylsilanyloxy)benzyl]-14-isopropyl-18-methoxy-17-methyl-3-oxa-9,12,15,28-tetraazatricyclo[21.3.1.15,9]octacosa-1(27),21,23,25-tetraene-4,10,13,16-tetraone (1381816-56-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

1.2: 16 h / 0 - 20 °C / Inert atmosphere

2.1: Grubbs catalyst first generation / dichloromethane / 16 h / Reflux

With N-ethyl-N,N-diisopropylamine; HATU; Grubbs catalyst first generation; In dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

3-Ethenylbenzyl alcohol

(S)-1-{(S)-2-((S)-2-amino-3-methylbutyrylamino)-3-[3-(tert-butyldimethylsilanyloxy)phenyl]propionyl}hexahydropyridazine-3-carboxylic acid 3-vinylbenzyl ester

(tert-butoxycarbonyl)-L-valine-L-(tert-butyldimethylsilyl)-meta-tyrosine-hexahydropyridazine-3S-carboxylic acid 2,2,2-trichloroethyl ester

(S)-1-{(S)-2-((S)-2-tert-butoxycarbonylamino-3-methylbutyrylamino)-3-[3-(tert-butyldimethylsilanyloxy)phenyl]propionyl}hexahydropyridazine-3-carboxylic acid 3-vinylbenzyl ester

Downstream raw materials:

(E)-(5S,11S,14S,17R,18R)-11-(3-hydroxybenzyl)-14-isopropyl-18-methoxy-17-methyl-3-oxa-9,12,15,28-tetraazatricyclo[21.3.1.1^5,9]octacosa-1⁽²⁷⁾,21,23,25-tetraene-4,10,13,16-tetraone

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