hept-6-en-1-oyl-L-valine-L-(tert-butyldimethylsilyl)-meta-tyrosine-hexahydropyridazine-3S-carboxylic acid 2,2,2-trichloroethyl ester

Base Information

• Chemical Name: hept-6-en-1-oyl-L-valine-L-(tert-butyldimethylsilyl)-meta-tyrosine-hexahydropyridazine-3S-carboxylic acid 2,2,2-trichloroethyl ester
• CAS No.: 247186-23-8
• Molecular Formula: C₃₄H₅₃Cl₃N₄O₆Si
• Molecular Weight: 748.263
• Mol file: 247186-23-8.mol

Synonyms:hept-6-en-1-oyl-L-valine-L-(tert-butyldimethylsilyl)-meta-tyrosine-hexahydropyridazine-3S-carboxylic acid 2,2,2-trichloroethyl ester

Chemical Property of hept-6-en-1-oyl-L-valine-L-(tert-butyldimethylsilyl)-meta-tyrosine-hexahydropyridazine-3S-carboxylic acid 2,2,2-trichloroethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of hept-6-en-1-oyl-L-valine-L-(tert-butyldimethylsilyl)-meta-tyrosine-hexahydropyridazine-3S-carboxylic acid 2,2,2-trichloroethyl ester

There total 15 articles about hept-6-en-1-oyl-L-valine-L-(tert-butyldimethylsilyl)-meta-tyrosine-hexahydropyridazine-3S-carboxylic acid 2,2,2-trichloroethyl 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: 70.0%

hept-6-enoic acid (1119-60-4) + (S)-1-{(S)-2-((S)-2-amino-3-methyl-butyrylamino)-3-[3-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionyl}-hexahydro-pyridazine-3-carboxylic acid 2,2,2-trichloro-ethyl ester → hept-6-en-1-oyl-L-valine-L-(tert-butyldimethylsilyl)-meta-tyrosine-hexahydropyridazine-3S-carboxylic acid 2,2,2-trichloroethyl ester (247186-23-8)

Guidance literature:

With 4-methyl-morpholine; isobutyl chloroformate; In tetrahydrofuran;

DOI:10.1002/(SICI)1521-3773(19990816)38:16<2443::AID-ANIE2443>3.0.CO;2-B

Reference yield:

3-benzyloxybenzyl bromide (1700-31-8) → hept-6-en-1-oyl-L-valine-L-(tert-butyldimethylsilyl)-meta-tyrosine-hexahydropyridazine-3S-carboxylic acid 2,2,2-trichloroethyl ester (247186-23-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

1.2: 62 percent / tetrahydrofuran; hexane / 1.5 h / -78 °C

2.1: 71 percent / aq. HCl / acetonitrile / 2 h / 20 °C

3.1: 8.85 g / tetrahydrofuran / -15 - 20 °C

4.1: 100 percent / aq. LiOH / tetrahydrofuran / 3 h / 0 °C

5.1: N-methylmorpholine / tetrahydrofuran / 0.5 h / -10 °C

6.1: 780 mg / N-methylmorpholine / tetrahydrofuran / -10 - 20 °C

7.1: H₂ / 10 percent Pd/C / propan-2-ol / 5 h

8.1: 5.4 g / imidazole / dimethylformamide / 16 h / 40 °C

9.1: TMSOTf / CH₂Cl₂ / 1 h / 0 °C

10.1: 2.98 g / tetrahydrofuran / 20 °C

With 4-methyl-morpholine; 1H-imidazole; hydrogenchloride; lithium hydroxide; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; hydrogen; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile;

DOI:10.1021/ja021327y

Reference yield:

(S)-3-(3-(benzyloxy)phenyl)-2-((S)-2-((tert-butoxycarbonyl)amino)-3-methylbutanamido)propanoic acid (222556-20-9) → hept-6-en-1-oyl-L-valine-L-(tert-butyldimethylsilyl)-meta-tyrosine-hexahydropyridazine-3S-carboxylic acid 2,2,2-trichloroethyl ester (247186-23-8)

Guidance literature:

Multi-step reaction with 6 steps

1: N-methylmorpholine / tetrahydrofuran / 0.5 h / -10 °C

2: 780 mg / N-methylmorpholine / tetrahydrofuran / -10 - 20 °C

3: H₂ / 10 percent Pd/C / propan-2-ol / 5 h

4: 5.4 g / imidazole / dimethylformamide / 16 h / 40 °C

5: TMSOTf / CH₂Cl₂ / 1 h / 0 °C

6: 2.98 g / tetrahydrofuran / 20 °C

With 4-methyl-morpholine; 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; hydrogen; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1021/ja021327y

upstream raw materials:

hept-6-enoic acid

t-Boc-L-valine

3-benzyloxybenzyl bromide

C₁₅H₂₇NO₆

Downstream raw materials:

(13E,15E)-(3S,6S,21S)-3-[3-(tert-Butyl-dimethyl-silanyloxy)-benzyl]-6-isopropyl-19-oxa-1,4,7,25-tetraaza-bicyclo[19.3.1]pentacosa-13,15-diene-2,5,8,20-tetraone

hept-6-en-1-oyl-L-valine-L-(tert-butyldimethylsilyl)-meta-tyrosine-hexahydropyridazine-3S-carboxylic acid hexa-3,5-dienyl ester