2-tert-butoxycarbonylamino-6-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoic acid 4-[9-(tert-butyl-diphenyl-silanyloxy)-3,7-dimethyl-nona-1,3,5,7-tetraenyl]-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-[9-(tert-butyl-diphenyl-silanyloxy)-3,7-dimethyl-nona-1,3,5,7-tetraenyl]-3,5,5-trimethyl-cyclohex-3-enyl ester
• CAS No.: 473758-69-9
• Molecular Formula: C₅₇H₈₂N₄O₇SSi
• Molecular Weight: 995.452
• Mol file: 473758-69-9.mol

Synonyms:2-tert-butoxycarbonylamino-6-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoic acid 4-[9-(tert-butyl-diphenyl-silanyloxy)-3,7-dimethyl-nona-1,3,5,7-tetraenyl]-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-[9-(tert-butyl-diphenyl-silanyloxy)-3,7-dimethyl-nona-1,3,5,7-tetraenyl]-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-[9-(tert-butyl-diphenyl-silanyloxy)-3,7-dimethyl-nona-1,3,5,7-tetraenyl]-3,5,5-trimethyl-cyclohex-3-enyl ester

There total 10 articles about 2-tert-butoxycarbonylamino-6-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoic acid 4-[9-(tert-butyl-diphenyl-silanyloxy)-3,7-dimethyl-nona-1,3,5,7-tetraenyl]-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: 78.0%

Boc-Lys(biotinyl)-OH (62062-43-5) + (R)-4-[(1E,3E,5Z,7E)-9-(tert-Butyl-diphenyl-silanyloxy)-3,7-dimethyl-nona-1,3,5,7-tetraenyl]-3,5,5-trimethyl-cyclohex-3-enol (473758-68-8) → 2-tert-butoxycarbonylamino-6-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoic acid 4-[9-(tert-butyl-diphenyl-silanyloxy)-3,7-dimethyl-nona-1,3,5,7-tetraenyl]-3,5,5-trimethyl-cyclohex-3-enyl ester (473758-69-9)

Guidance literature:

With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; dimethyl sulfoxide; for 20h;

DOI:10.1016/S0040-4020(02)00667-1

Reference yield:

(4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexan-1-one (20548-02-1,55058-51-0,60686-81-9,60686-82-0,82977-53-5,90082-06-7,90129-05-8,99881-84-2,60046-50-6) → 2-tert-butoxycarbonylamino-6-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoic acid 4-[9-(tert-butyl-diphenyl-silanyloxy)-3,7-dimethyl-nona-1,3,5,7-tetraenyl]-3,5,5-trimethyl-cyclohex-3-enyl ester (473758-69-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 97 percent / DMAP; triethylamine / CH₂Cl₂

2.1: 68 percent / LDA

3.1: 67 percent / PdCl₂(PPh₃)2 / dimethylformamide / 30 h / 80 °C

4.1: n-BuLi / tetrahydrofuran / 0 - 20 °C

4.2: 99 percent / tetrahydrofuran / 2 h / 20 °C

5.1: 99 percent / TBAF / tetrahydrofuran / 0 - 20 °C

6.1: 432 mg / i-PrNH₂; CuI / tetrakis(triphenylphosphine)palladium / 2 h / 20 °C

7.1: 99 percent / Zn; Cu(OAc)2; AgNO₃ / H₂O; methanol / 24 h / 20 °C

8.1: 78 percent / EDC; DMAP / CH₂Cl₂; dimethylsulfoxide / 20 h

With dmap; copper(l) iodide; n-butyllithium; copper diacetate; tetrabutyl ammonium fluoride; silver nitrate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; isopropylamine; triethylamine; zinc; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 3.1: Heck reaction / 4.2: Horner-Wadsworth-Emmons reaction / 6.1: Sonogashira coupling;

DOI:10.1016/S0040-4020(02)00667-1

Reference yield:

(6R)-levodione (60046-49-3) → 2-tert-butoxycarbonylamino-6-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoic acid 4-[9-(tert-butyl-diphenyl-silanyloxy)-3,7-dimethyl-nona-1,3,5,7-tetraenyl]-3,5,5-trimethyl-cyclohex-3-enyl ester (473758-69-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 66 percent / Raney Nickel

2.1: 97 percent / DMAP; triethylamine / CH₂Cl₂

3.1: 68 percent / LDA

4.1: 67 percent / PdCl₂(PPh₃)2 / dimethylformamide / 30 h / 80 °C

5.1: n-BuLi / tetrahydrofuran / 0 - 20 °C

5.2: 99 percent / tetrahydrofuran / 2 h / 20 °C

6.1: 99 percent / TBAF / tetrahydrofuran / 0 - 20 °C

7.1: 432 mg / i-PrNH₂; CuI / tetrakis(triphenylphosphine)palladium / 2 h / 20 °C

8.1: 99 percent / Zn; Cu(OAc)2; AgNO₃ / H₂O; methanol / 24 h / 20 °C

9.1: 78 percent / EDC; DMAP / CH₂Cl₂; dimethylsulfoxide / 20 h

With dmap; copper(l) iodide; n-butyllithium; copper diacetate; tetrabutyl ammonium fluoride; nickel; silver nitrate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; isopropylamine; triethylamine; zinc; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 4.1: Heck reaction / 5.2: Horner-Wadsworth-Emmons reaction / 7.1: Sonogashira coupling;

DOI:10.1016/S0040-4020(02)00667-1

upstream raw materials:

Boc-Lys(biotinyl)-OH

(R)-4-[(1E,3E,5Z,7E)-9-(tert-Butyl-diphenyl-silanyloxy)-3,7-dimethyl-nona-1,3,5,7-tetraenyl]-3,5,5-trimethyl-cyclohex-3-enol

(4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexan-1-one

(6R)-levodione

Downstream raw materials:

3-[N⁶-biotinyl-N²-(tert-butoxycarbonyl)-L-lysyloxy]-11-cis-retinol