Trimethylsilanyl-acetic acid (2R,4S,9aR)-4-(5'-formyl-4,5,2'-trimethoxy-biphenyl-2-yl)-octahydro-quinolizin-2-yl ester

Base Information

• Chemical Name: Trimethylsilanyl-acetic acid (2R,4S,9aR)-4-(5'-formyl-4,5,2'-trimethoxy-biphenyl-2-yl)-octahydro-quinolizin-2-yl ester
• CAS No.: 82504-10-7
• Molecular Formula: C₃₀H₄₁NO₆Si
• Molecular Weight: 539.744
• Mol file: 82504-10-7.mol

Synonyms:Trimethylsilanyl-acetic acid (2R,4S,9aR)-4-(5'-formyl-4,5,2'-trimethoxy-biphenyl-2-yl)-octahydro-quinolizin-2-yl ester

Chemical Property of Trimethylsilanyl-acetic acid (2R,4S,9aR)-4-(5'-formyl-4,5,2'-trimethoxy-biphenyl-2-yl)-octahydro-quinolizin-2-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Trimethylsilanyl-acetic acid (2R,4S,9aR)-4-(5'-formyl-4,5,2'-trimethoxy-biphenyl-2-yl)-octahydro-quinolizin-2-yl ester

There total 7 articles about Trimethylsilanyl-acetic acid (2R,4S,9aR)-4-(5'-formyl-4,5,2'-trimethoxy-biphenyl-2-yl)-octahydro-quinolizin-2-yl 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: 60.0%

trimetylsilylketene (4071-85-6) + 2'-((2R,4S,9aR)-2-Hydroxy-octahydro-quinolizin-4-yl)-6,4',5'-trimethoxy-biphenyl-3-carbaldehyde (82504-09-4) → Trimethylsilanyl-acetic acid (2R,4S,9aR)-4-(5'-formyl-4,5,2'-trimethoxy-biphenyl-2-yl)-octahydro-quinolizin-2-yl ester (82504-10-7)

Guidance literature:

In tetrahydrofuran; at -20 ℃; for 40h;

DOI:10.1016/S0040-4039(00)87127-0

Reference yield:

2-bromo-4,5-dimethoxybenzaldehyde (5392-10-9) → Trimethylsilanyl-acetic acid (2R,4S,9aR)-4-(5'-formyl-4,5,2'-trimethoxy-biphenyl-2-yl)-octahydro-quinolizin-2-yl ester (82504-10-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 30 percent / naphthalene / Cu bronze / 2 h / 220 °C

2: 1.) aq. NaOH / 1.) THF, MeOH room temp. 48 h; 2.) MeOH, reflux, 4 h

3: 93 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 12 h / -78 - 20 °C

4: 60 percent / tetrahydrofuran / 40 h / -20 °C

With sodium hydroxide; naphthalene; L-Selectride; copper bronze; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)87127-0

Reference yield:

2-iodo-4-cyanophenol (2296-23-3) → Trimethylsilanyl-acetic acid (2R,4S,9aR)-4-(5'-formyl-4,5,2'-trimethoxy-biphenyl-2-yl)-octahydro-quinolizin-2-yl ester (82504-10-7)

Guidance literature:

Multi-step reaction with 5 steps

1: K₂CO₃ / acetone

2: 30 percent / naphthalene / Cu bronze / 2 h / 220 °C

3: 1.) aq. NaOH / 1.) THF, MeOH room temp. 48 h; 2.) MeOH, reflux, 4 h

4: 93 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 12 h / -78 - 20 °C

5: 60 percent / tetrahydrofuran / 40 h / -20 °C

With sodium hydroxide; naphthalene; L-Selectride; potassium carbonate; copper bronze; In tetrahydrofuran; acetone;

DOI:10.1016/S0040-4039(00)87127-0

upstream raw materials:

trimetylsilylketene

2'-((2R,4S,9aR)-2-Hydroxy-octahydro-quinolizin-4-yl)-6,4',5'-trimethoxy-biphenyl-3-carbaldehyde

2-bromo-4,5-dimethoxybenzaldehyde

2-iodo-4-cyanophenol

Downstream raw materials:

d,l-17-O-methyllythridine