(E)-4-(4-Methoxy-phenyl)-2-oxo-but-3-enoic acid (3R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-5-oxo-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: (E)-4-(4-Methoxy-phenyl)-2-oxo-but-3-enoic acid (3R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-5-oxo-tetrahydro-furan-3-yl ester
• CAS No.: 188251-24-3
• Molecular Formula: C₃₁H₃₂O₇Si
• Molecular Weight: 544.676
• Mol file: 188251-24-3.mol

Synonyms:(E)-4-(4-Methoxy-phenyl)-2-oxo-but-3-enoic acid (3R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-5-oxo-tetrahydro-furan-3-yl ester

Chemical Property of (E)-4-(4-Methoxy-phenyl)-2-oxo-but-3-enoic acid (3R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-5-oxo-tetrahydro-furan-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-4-(4-Methoxy-phenyl)-2-oxo-but-3-enoic acid (3R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-5-oxo-tetrahydro-furan-3-yl ester

There total 2 articles about (E)-4-(4-Methoxy-phenyl)-2-oxo-but-3-enoic acid (3R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-5-oxo-tetrahydro-furan-3-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: 95.0%

(E)-4-(4-methoxy-phenyl)-2-oxo-3-butenoic acid (17451-21-7,128935-12-6) + (3R,4R)-3-(tert-Butyl-diphenyl-silanyloxy)-4-hydroxy-dihydro-furan-2-one (188251-56-1) → (E)-4-(4-Methoxy-phenyl)-2-oxo-but-3-enoic acid (3R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-5-oxo-tetrahydro-furan-3-yl ester (188251-24-3)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; 0 deg C, 5 h; r.t., 10 h;

DOI:10.1016/S0040-4039(97)00144-5

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (E)-4-(4-Methoxy-phenyl)-2-oxo-but-3-enoic acid (3R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-5-oxo-tetrahydro-furan-3-yl ester (188251-24-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

2: 95 percent / DMAP, DCC / CH₂Cl₂ / 12 h / Ambient temperature

With 1H-imidazole; dmap; dicyclohexyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(97)00646-7

Reference yield: 76.0%

4-Methoxystyrene (637-69-4,24936-44-5) + (E)-4-(4-Methoxy-phenyl)-2-oxo-but-3-enoic acid (3R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-5-oxo-tetrahydro-furan-3-yl ester (188251-24-3) → 4,6-Bis-(4-methoxy-phenyl)-5,6-dihydro-4H-pyran-2-carboxylic acid (3R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-5-oxo-tetrahydro-furan-3-yl ester

Guidance literature:

Eu(fod)3; hexane, 60 deg C, 3 d; toluene, 60 deg C, 3 d;

DOI:10.1016/S0040-4039(97)00144-5

upstream raw materials:

(E)-4-(4-methoxy-phenyl)-2-oxo-3-butenoic acid

(3R,4R)-3-(tert-Butyl-diphenyl-silanyloxy)-4-hydroxy-dihydro-furan-2-one

tert-butylchlorodiphenylsilane

Downstream raw materials:

(-)-sugiresinol dimethyl ether

(2R,4R)-2,4-Bis-(4-methoxy-phenyl)-3,4-dihydro-2H-pyran

(2S,4R,6R)-4,6-Bis-(4-methoxy-phenyl)-tetrahydro-pyran-2-carboxylic acid