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

Base Information

• Chemical Name: hept-6-en-1-oyl-L-valine-L-(tert-butyldimethylsilyl)-meta-tyrosine-hexahydropyridazine-3S-carboxylic acid hexa-3,5-dienyl ester
• CAS No.: 247186-24-9
• Molecular Formula: C₃₈H₆₀N₄O₆Si
• Molecular Weight: 697.003
• Mol file: 247186-24-9.mol

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

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

There total 17 articles about hept-6-en-1-oyl-L-valine-L-(tert-butyldimethylsilyl)-meta-tyrosine-hexahydropyridazine-3S-carboxylic acid hexa-3,5-dienyl 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: 82.0%

(E)-hexa-3,5-dien-1-ol (73670-87-8) + (S)-1-[(S)-3-[3-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-((S)-2-hept-6-enoylamino-3-methyl-butyrylamino)-propionyl]-hexahydro-pyridazine-3-carboxylic acid → hept-6-en-1-oyl-L-valine-L-(tert-butyldimethylsilyl)-meta-tyrosine-hexahydropyridazine-3S-carboxylic acid hexa-3,5-dienyl ester (247186-24-9)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; 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 hexa-3,5-dienyl ester (247186-24-9)

Guidance literature:

Multi-step reaction with 12 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

11.1: Zn; aq. NH₄OAc / tetrahydrofuran / 20 °C

12.1: 230 mg / Ph₃P; diethylazodicarboxylate / tetrahydrofuran / 20 °C

With 4-methyl-morpholine; 1H-imidazole; hydrogenchloride; lithium hydroxide; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; ammonium acetate; hydrogen; triphenylphosphine; zinc; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile; 12.1: Mitsunobu reaction;

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 hexa-3,5-dienyl ester (247186-24-9)

Guidance literature:

Multi-step reaction with 8 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

7: Zn; aq. NH₄OAc / tetrahydrofuran / 20 °C

8: 230 mg / Ph₃P; diethylazodicarboxylate / tetrahydrofuran / 20 °C

With 4-methyl-morpholine; 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; ammonium acetate; hydrogen; triphenylphosphine; zinc; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; 8: Mitsunobu reaction;

DOI:10.1021/ja021327y

upstream raw materials:

(E)-hexa-3,5-dien-1-ol

t-Boc-L-valine

hept-6-enoic acid

3-benzyloxybenzyl bromide

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