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

Base Information

• Chemical Name: (S)-1-{(S)-2-((S)-2-tert-butoxycarbonylamino-3-methylbutyrylamino)-3-[3-(tert-butyldimethylsilanyloxy)phenyl]propionyl}hexahydropyridazine-3-carboxylic acid 3-vinylbenzyl ester
• CAS No.: 1381811-94-4
• Molecular Formula: C₃₉H₅₈N₄O₇Si
• Molecular Weight: 722.998
• Mol file: 1381811-94-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

3-ethenylbenzaldehyde (19955-99-8) → (S)-1-{(S)-2-((S)-2-tert-butoxycarbonylamino-3-methylbutyrylamino)-3-[3-(tert-butyldimethylsilanyloxy)phenyl]propionyl}hexahydropyridazine-3-carboxylic acid 3-vinylbenzyl ester (1381811-94-4)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate / methanol / 0.25 h / 20 °C / Inert atmosphere

2: sodium hydride / tetrahydrofuran; mineral oil / 6 h / 40 °C / Inert atmosphere

With sodium tetrahydroborate; sodium hydride; In tetrahydrofuran; methanol; mineral oil;

DOI:10.1021/acs.jmedchem.6b01329

Reference yield:

(S)-1-{(S)-2-((S)-2-tert-butoxycarbonylamino-3-methylbutyrylamino)-3-[3-(tert-butyldimethylsilanyloxy)phenyl]propionyl}hexahydropyridazine-3-carboxylic acid 3-vinylbenzyl ester (1381811-94-4) → (S)-1-{(S)-2-((S)-2-amino-3-methylbutyrylamino)-3-[3-(tert-butyldimethylsilanyloxy)phenyl]propionyl}hexahydropyridazine-3-carboxylic acid 3-vinylbenzyl ester (1381812-31-2)

Guidance literature:

(S)-1-{(S)-2-((S)-2-tert-butoxycarbonylamino-3-methylbutyrylamino)-3-[3-(tert-butyldimethylsilanyloxy)phenyl]propionyl}hexahydropyridazine-3-carboxylic acid 3-vinylbenzyl ester; With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 1.5h;

With N-ethyl-N,N-diisopropylamine; In dichloromethane; Product distribution / selectivity;

Reference yield:

(S)-1-{(S)-2-((S)-2-tert-butoxycarbonylamino-3-methylbutyrylamino)-3-[3-(tert-butyldimethylsilanyloxy)phenyl]propionyl}hexahydropyridazine-3-carboxylic acid 3-vinylbenzyl ester (1381811-94-4) → (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:

Multi-step reaction with 3 steps

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

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

2.2: 16 h / 0 - 20 °C / Inert atmosphere

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

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

upstream raw materials:

3-ethenylbenzaldehyde

Downstream raw materials:

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

(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

(E)-(5S,11S,14S,17R,18R)-18-ethoxy-11-(3-hydroxy-benzyl)-14-isopropyl-17-methyl-3-oxa-9,12,15,28-tetraaza-tricyclo[21.3.1.1*5,9*]octacosa-1⁽²⁶⁾,21,23⁽²⁷⁾,24-tetraene-4,10,13,16-tetraone

(E)-(5S,11S,14S,17R,18R)-11-[3-(tert-butyl-dimethyl-silanyloxy)-benzyl]-18-ethoxy-14-isopropyl-17-methyl-3-oxa-9,12,15,28-tetraaza-tricyclo[21.3.1.1*5,9*]octacosa-1⁽²⁶⁾,21,23⁽²⁷⁾,24-tetraene-4,10,13,16-tetraone