(+/-)-tert-butyl 2-O-(4-tert-butyldimethylsilylcoumaroyl)-3-(4-tert-butyldimethylsilyloxyphenyl)lactate

Base Information

• Chemical Name: (+/-)-tert-butyl 2-O-(4-tert-butyldimethylsilylcoumaroyl)-3-(4-tert-butyldimethylsilyloxyphenyl)lactate
• CAS No.: 395098-96-1
• Molecular Formula: C₃₄H₅₂O₆Si₂
• Molecular Weight: 612.954
• Mol file: 395098-96-1.mol

Synonyms:(+/-)-tert-butyl 2-O-(4-tert-butyldimethylsilylcoumaroyl)-3-(4-tert-butyldimethylsilyloxyphenyl)lactate

Chemical Property of (+/-)-tert-butyl 2-O-(4-tert-butyldimethylsilylcoumaroyl)-3-(4-tert-butyldimethylsilyloxyphenyl)lactate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-tert-butyl 2-O-(4-tert-butyldimethylsilylcoumaroyl)-3-(4-tert-butyldimethylsilyloxyphenyl)lactate

There total 5 articles about (+/-)-tert-butyl 2-O-(4-tert-butyldimethylsilylcoumaroyl)-3-(4-tert-butyldimethylsilyloxyphenyl)lactate 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: 33.0%

(E)-3-(4'-((tert-butyldimethylsilyl)oxy)phenyl)acrylic acid (141222-28-8) + (+/-)-tert-butyl 3-(4-tert-butyldimethylsilyloxyphenyl)lactate (395098-95-0) → (+/-)-tert-butyl 2-O-(4-tert-butyldimethylsilylcoumaroyl)-3-(4-tert-butyldimethylsilyloxyphenyl)lactate (395098-96-1)

Guidance literature:

With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 40h;

DOI:10.1248/cpb.49.1644

Reference yield:

p-Coumaric Acid (7400-08-0,50940-26-6) → (+/-)-tert-butyl 2-O-(4-tert-butyldimethylsilylcoumaroyl)-3-(4-tert-butyldimethylsilyloxyphenyl)lactate (395098-96-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / imidazole / dimethylformamide / 3 h / 20 °C

2: 33 percent / HBT; EDCI; DMAP / CH₂Cl₂ / 40 h / 20 °C

With 1H-imidazole; dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.49.1644

Reference yield:

2-hydroxy-3-(4-hydroxyphenyl)propanoic acid (6482-98-0,23508-35-2,89919-57-3,306-23-0) → (+/-)-tert-butyl 2-O-(4-tert-butyldimethylsilylcoumaroyl)-3-(4-tert-butyldimethylsilyloxyphenyl)lactate (395098-96-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / tetrahydrofuran; 2-methyl-propan-2-ol / 14 h / 20 °C

2: 72 percent / DMAP; Et₃N / tetrahydrofuran / 14 h / 20 °C

3: 33 percent / HBT; EDCI; DMAP / CH₂Cl₂ / 40 h / 20 °C

With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; dichloromethane; tert-butyl alcohol;

DOI:10.1248/cpb.49.1644

upstream raw materials:

(E)-3-(4'-((tert-butyldimethylsilyl)oxy)phenyl)acrylic acid

(+/-)-tert-butyl 3-(4-tert-butyldimethylsilyloxyphenyl)lactate

p-Coumaric Acid

2-hydroxy-3-(4-hydroxyphenyl)propanoic acid

Downstream raw materials:

(+/-)-tert-butyl 2-O-(4-coumaroyl)-3-(4-hydroxyphenyl)lactate