(diethoxy-phosphoryl)-acetic acid 5-(4-methoxy-benzyloxy)-2-oxo-cyclohex-3-enyl ester

Base Information

• Chemical Name: (diethoxy-phosphoryl)-acetic acid 5-(4-methoxy-benzyloxy)-2-oxo-cyclohex-3-enyl ester
• CAS No.: 748154-83-8
• Molecular Formula: C₂₀H₂₇O₈P
• Molecular Weight: 426.403
• Mol file: 748154-83-8.mol

Synonyms:(diethoxy-phosphoryl)-acetic acid 5-(4-methoxy-benzyloxy)-2-oxo-cyclohex-3-enyl ester

Chemical Property of (diethoxy-phosphoryl)-acetic acid 5-(4-methoxy-benzyloxy)-2-oxo-cyclohex-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (diethoxy-phosphoryl)-acetic acid 5-(4-methoxy-benzyloxy)-2-oxo-cyclohex-3-enyl ester

There total 20 articles about (diethoxy-phosphoryl)-acetic acid 5-(4-methoxy-benzyloxy)-2-oxo-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: 42.0%

triethyl phosphite (122-52-1) + Bromo-acetic acid (1R,5S)-5-(4-methoxy-benzyloxy)-2-oxo-cyclohex-3-enyl ester (748154-82-7) → (diethoxy-phosphoryl)-acetic acid 5-(4-methoxy-benzyloxy)-2-oxo-cyclohex-3-enyl ester (748154-83-8)

Guidance literature:

DOI:10.1016/j.tetlet.2004.05.129

Reference yield:

6-hydroxy-4-(4-methoxy-benzyloxy)-cyclohex-2-enone (863997-72-2) + diethylphosphonoacetic acid (3095-95-2) → (diethoxy-phosphoryl)-acetic acid 5-(4-methoxy-benzyloxy)-2-oxo-cyclohex-3-enyl ester + (diethoxy-phosphoryl)-acetic acid 5-(4-methoxy-benzyloxy)-2-oxo-cyclohex-3-enyl ester (748154-83-8)

Guidance literature:

With diethylazodicarboxylate; 4-(N,N-Dimethylamino)triphenylphosphine; In toluene; benzene; at 0 - 20 ℃; for 1.5h; Title compound not separated from byproducts;

DOI:10.1016/j.tet.2006.05.022

Reference yield:

(2S,3S,5S,6S)-2-Iodomethyl-6-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol (748154-79-2) → (diethoxy-phosphoryl)-acetic acid 5-(4-methoxy-benzyloxy)-2-oxo-cyclohex-3-enyl ester (748154-83-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 99 percent / CH₂Cl₂ / 0.5 h / 0 °C

2: 99 percent / t-BuOK / tetrahydrofuran / 15 h / 20 °C

3: 70 percent / Hg(OCOCF₃)2 / acetone; H₂O / 9 h / 0 °C

4: 100 percent / triethylamine; mesyl chloride / CH₂Cl₂ / 1 h / 0 - 20 °C

5: 100 percent / AcOH; TBAF / tetrahydrofuran / 46 h / 0 - 20 °C

6: DEAD; N-[4-(diphenylphosphino)phenyl]-N,N-dimethylamine / benzene; toluene / 1.5 h / 0 - 20 °C

With potassium tert-butylate; tetrabutyl ammonium fluoride; mercury(II) trifluoroacetate; acetic acid; methanesulfonyl chloride; triethylamine; diethylazodicarboxylate; 4-(N,N-Dimethylamino)triphenylphosphine; In tetrahydrofuran; dichloromethane; water; acetone; toluene; benzene; 3: Ferrier carbocyclization / 6: Mitsunobu reaction;

DOI:10.1016/j.tet.2006.05.022

upstream raw materials:

triethyl phosphite

Bromo-acetic acid (1R,5S)-5-(4-methoxy-benzyloxy)-2-oxo-cyclohex-3-enyl ester

6-hydroxy-4-(4-methoxy-benzyloxy)-cyclohex-2-enone

diethylphosphonoacetic acid

Downstream raw materials:

(6S,7aR)-6-hydroxy-7,7a-dihydrobenzofuran-2(6H)-one

6-(4-methoxy-benzyloxy)-7,7a-dihydro-6H-benzofuran-2-one