2-tert-butoxycarbonylamino-6-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoic acid 4-(3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethylidene]-cyclohept-2-enylidene}-but-1-enyl)-3,5,5-trimethyl-cyclohex-3-enyl ester

Base Information

• Chemical Name: 2-tert-butoxycarbonylamino-6-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoic acid 4-(3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethylidene]-cyclohept-2-enylidene}-but-1-enyl)-3,5,5-trimethyl-cyclohex-3-enyl ester
• CAS No.: 922174-32-1
• Molecular Formula: C₄₉H₈₀N₄O₇SSi
• Molecular Weight: 897.348
• Mol file: 922174-32-1.mol

Synonyms:2-tert-butoxycarbonylamino-6-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoic acid 4-(3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethylidene]-cyclohept-2-enylidene}-but-1-enyl)-3,5,5-trimethyl-cyclohex-3-enyl ester

Chemical Property of 2-tert-butoxycarbonylamino-6-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoic acid 4-(3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethylidene]-cyclohept-2-enylidene}-but-1-enyl)-3,5,5-trimethyl-cyclohex-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-tert-butoxycarbonylamino-6-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoic acid 4-(3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethylidene]-cyclohept-2-enylidene}-but-1-enyl)-3,5,5-trimethyl-cyclohex-3-enyl ester

There total 17 articles about 2-tert-butoxycarbonylamino-6-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoic acid 4-(3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethylidene]-cyclohept-2-enylidene}-but-1-enyl)-3,5,5-trimethyl-cyclohex-3-enyl 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:

4-(3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethylidene]-cyclohept-2-enylidene}-but-1-enyl)-3,5,5-trimethyl-cyclohex-3-enol (922174-38-7) + Boc-Lys(biotinyl)-OH (62062-43-5) → 2-tert-butoxycarbonylamino-6-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoic acid 4-(3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethylidene]-cyclohept-2-enylidene}-but-1-enyl)-3,5,5-trimethyl-cyclohex-3-enyl ester (922174-32-1)

Guidance literature:

With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at 0 - 20 ℃;

DOI:10.1139/V06-092

Reference yield:

acetic acid 4-bromomethyl-3,5,5-trimethyl-cyclohex-3-enyl ester (922174-25-2) → 2-tert-butoxycarbonylamino-6-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoic acid 4-(3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethylidene]-cyclohept-2-enylidene}-but-1-enyl)-3,5,5-trimethyl-cyclohex-3-enyl ester (922174-32-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 1.37 g / benzene / 12 h / Heating

2.1: n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C

2.2: 40 percent / tetrahydrofuran; hexane / 14 h / 20 °C

3.1: 63 percent / 4-(dimethylamino)pyridine; pyridine / 12 h / 20 °C

4.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 - 20 °C

5.1: 84 percent / MnO₂ / CH₂Cl₂ / 0 - 20 °C

6.1: NaH / tetrahydrofuran / 0 - 20 °C

6.2: 27 percent / tetrahydrofuran / 12 h / 20 °C

7.1: 82 percent / diisobutylaluminum hydride / diethyl ether; toluene / 0.67 h / 0 °C

8.1: 50 percent / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 - 20 °C

9.1: sodium borohydride / CHCl₃; methanol / 0.03 h / -10 °C

10.1: 13.4 mg / imidazole / CH₂Cl₂ / 2 h / 0 °C

11.1: K₂CO₃ / methanol / 0 - 20 °C

12.1: 7.8 mg / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 - 20 °C

With pyridine; 1H-imidazole; dmap; manganese(IV) oxide; sodium tetrahydroborate; n-butyllithium; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; chloroform; toluene; benzene; 2.2: Wittig reaction / 6.2: Horner-Emmons-Wadsworth reaction;

DOI:10.1139/V06-092

Reference yield:

acetic acid 4-hydroxymethyl-3,5,5-trimethyl-cyclohex-3-enyl ester (922174-24-1) → 2-tert-butoxycarbonylamino-6-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoic acid 4-(3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethylidene]-cyclohept-2-enylidene}-but-1-enyl)-3,5,5-trimethyl-cyclohex-3-enyl ester (922174-32-1)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 94 percent / triphenylphosphine; carbon tetrabromide / 1 h / 20 °C

2.1: 1.37 g / benzene / 12 h / Heating

3.1: n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C

3.2: 40 percent / tetrahydrofuran; hexane / 14 h / 20 °C

4.1: 63 percent / 4-(dimethylamino)pyridine; pyridine / 12 h / 20 °C

5.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 - 20 °C

6.1: 84 percent / MnO₂ / CH₂Cl₂ / 0 - 20 °C

7.1: NaH / tetrahydrofuran / 0 - 20 °C

7.2: 27 percent / tetrahydrofuran / 12 h / 20 °C

8.1: 82 percent / diisobutylaluminum hydride / diethyl ether; toluene / 0.67 h / 0 °C

9.1: 50 percent / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 - 20 °C

10.1: sodium borohydride / CHCl₃; methanol / 0.03 h / -10 °C

11.1: 13.4 mg / imidazole / CH₂Cl₂ / 2 h / 0 °C

12.1: K₂CO₃ / methanol / 0 - 20 °C

13.1: 7.8 mg / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 - 20 °C

With pyridine; 1H-imidazole; dmap; manganese(IV) oxide; sodium tetrahydroborate; n-butyllithium; carbon tetrabromide; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; chloroform; toluene; benzene; 3.2: Wittig reaction / 7.2: Horner-Emmons-Wadsworth reaction;

DOI:10.1139/V06-092

upstream raw materials:

4-(3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethylidene]-cyclohept-2-enylidene}-but-1-enyl)-3,5,5-trimethyl-cyclohex-3-enol

Boc-Lys(biotinyl)-OH

acetic acid 4-bromomethyl-3,5,5-trimethyl-cyclohex-3-enyl ester

acetic acid 4-hydroxymethyl-3,5,5-trimethyl-cyclohex-3-enyl ester

Downstream raw materials:

2-tert-butoxycarbonylamino-6-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoic acid 4-{3-[4-(2-hydroxy-ethylidene)-cyclohept-2-enylidene]-but-1-enyl}-3,5,5-trimethyl-cyclohex-3-enyl ester