N-(2,2-dimethoxy-ethyl)-N-(1-formyl-4-triisopropylsilanyloxy-cyclohex-3-enyl)-acetamide

Base Information

• Chemical Name: N-(2,2-dimethoxy-ethyl)-N-(1-formyl-4-triisopropylsilanyloxy-cyclohex-3-enyl)-acetamide
• CAS No.: 342776-32-3
• Molecular Formula: C₂₂H₄₁NO₅Si
• Molecular Weight: 427.657
• Mol file: 342776-32-3.mol

Synonyms:N-(2,2-dimethoxy-ethyl)-N-(1-formyl-4-triisopropylsilanyloxy-cyclohex-3-enyl)-acetamide

Chemical Property of N-(2,2-dimethoxy-ethyl)-N-(1-formyl-4-triisopropylsilanyloxy-cyclohex-3-enyl)-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(2,2-dimethoxy-ethyl)-N-(1-formyl-4-triisopropylsilanyloxy-cyclohex-3-enyl)-acetamide

There total 2 articles about N-(2,2-dimethoxy-ethyl)-N-(1-formyl-4-triisopropylsilanyloxy-cyclohex-3-enyl)-acetamide 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: 64.0%

2-(triisopropylsiloxy)-1,3-butadiene (139278-54-9) + N-(2,2-dimethoxy-ethyl)-N-(2,2-dimethyl-4H-[1,3]dioxin-5-yl)-acetamide (342776-33-4) → N-(2,2-dimethoxy-ethyl)-N-(6-triisopropylsilanyloxy-6-vinyl-5,6-dihydro-4H-pyran-3-yl)-acetamide + N-(2,2-dimethoxy-ethyl)-N-(1-formyl-4-triisopropylsilanyloxy-cyclohex-3-enyl)-acetamide (342776-32-3)

Guidance literature:

With 2,6-di-tert-butyl-4-methyl-phenol; methyloxirane; In benzonitrile; at 120 ℃; for 16h;

DOI:10.1021/ol015506g

Reference yield:

(2,2-dimethoxy-ethyl)-(2,2-dimethyl-4H-[1,3]dioxin-5-yl)-amine → N-(2,2-dimethoxy-ethyl)-N-(1-formyl-4-triisopropylsilanyloxy-cyclohex-3-enyl)-acetamide (342776-32-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 5.96 g / Et₃N / benzene / 0 - 20 °C

2: 64 percent / BHT; propylene oxide / benzonitrile / 16 h / 120 °C

With 2,6-di-tert-butyl-4-methyl-phenol; triethylamine; methyloxirane; In benzonitrile; benzene; 2: retro-Diels-Alder reaction;

DOI:10.1021/ol015506g

Reference yield:

N-(2,2-dimethoxy-ethyl)-N-(1-formyl-4-triisopropylsilanyloxy-cyclohex-3-enyl)-acetamide (342776-32-3) → (1R,6R,8R,9R)-9-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyl)-5-aza-tricyclo[6.3.1.01,5]dodec-2-ene-4,7-dione

Guidance literature:

Multi-step reaction with 7 steps

1.1: potassium t-butoxide; ethyl acetate / tetrahydrofuran / 0.67 h / 0 °C

2.1: 4.72 g / trifluoroacetic acid / H₂O / 4 h / 0 - 20 °C

3.1: 92 percent / sodium borohydride / acetic acid / 0.5 h / 20 °C

4.1: imidazole / dimethylformamide / 20 °C

5.1: 93 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

6.1: 98 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 °C

7.1: KOBu-t / tetrahydrofuran / 0.33 h / 0 °C

7.2: 97 percent / tetrahydrofuran; dimethylformamide / 0.33 h / 0 °C

With 1H-imidazole; sodium tetrahydroborate; oxalyl dichloride; potassium tert-butylate; tetrabutyl ammonium fluoride; dimethyl sulfoxide; ethyl acetate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; 6.1: Swern oxidation;

DOI:10.1021/ol015506g

upstream raw materials:

2-(triisopropylsiloxy)-1,3-butadiene

N-(2,2-dimethoxy-ethyl)-N-(2,2-dimethyl-4H-[1,3]dioxin-5-yl)-acetamide