(diethoxy-phosphoryl)-acetic acid 3-(4-methoxy-benzyl)-4-[4-(4-methoxy-benzyloxy)-butyl]-6-oxo-2-oxa-3-aza-bicyclo[3.3.1]non-7-en-5-yl ester

Base Information

• Chemical Name: (diethoxy-phosphoryl)-acetic acid 3-(4-methoxy-benzyl)-4-[4-(4-methoxy-benzyloxy)-butyl]-6-oxo-2-oxa-3-aza-bicyclo[3.3.1]non-7-en-5-yl ester
• CAS No.: 916728-21-7
• Molecular Formula: C₃₃H₄₄NO₁₀P
• Molecular Weight: 645.687
• Mol file: 916728-21-7.mol

Synonyms:(diethoxy-phosphoryl)-acetic acid 3-(4-methoxy-benzyl)-4-[4-(4-methoxy-benzyloxy)-butyl]-6-oxo-2-oxa-3-aza-bicyclo[3.3.1]non-7-en-5-yl ester

Chemical Property of (diethoxy-phosphoryl)-acetic acid 3-(4-methoxy-benzyl)-4-[4-(4-methoxy-benzyloxy)-butyl]-6-oxo-2-oxa-3-aza-bicyclo[3.3.1]non-7-en-5-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (diethoxy-phosphoryl)-acetic acid 3-(4-methoxy-benzyl)-4-[4-(4-methoxy-benzyloxy)-butyl]-6-oxo-2-oxa-3-aza-bicyclo[3.3.1]non-7-en-5-yl ester

There total 9 articles about (diethoxy-phosphoryl)-acetic acid 3-(4-methoxy-benzyl)-4-[4-(4-methoxy-benzyloxy)-butyl]-6-oxo-2-oxa-3-aza-bicyclo[3.3.1]non-7-en-5-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: 71.0%

5-hydroxy-3-(4-methoxy-benzyl)-4-[4-(4-methoxy-benzyloxy)-butyl]-2-oxa-3-aza-bicyclo[3.3.1]non-7-en-6-one (916728-20-6) + diethylphosphonoacetic acid (3095-95-2) → (diethoxy-phosphoryl)-acetic acid 3-(4-methoxy-benzyl)-4-[4-(4-methoxy-benzyloxy)-butyl]-6-oxo-2-oxa-3-aza-bicyclo[3.3.1]non-7-en-5-yl ester (916728-21-7)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1002/anie.200602569

Reference yield:

7-(4-methoxy-benzyl)-6-[4-(4-methoxy-benzyloxy)-butyl]-2,2-dimethyl-9-vinyl-1,3,8-trioxa-7-aza-spiro[4.5]decane (916728-16-0) → (diethoxy-phosphoryl)-acetic acid 3-(4-methoxy-benzyl)-4-[4-(4-methoxy-benzyloxy)-butyl]-6-oxo-2-oxa-3-aza-bicyclo[3.3.1]non-7-en-5-yl ester (916728-21-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 93 percent / aq. HCl / tetrahydrofuran / 48 h

2: 64 percent / o-iodobenzoic acid; dimethyl sulfoxide / 2 h / 20 °C

3: 76 percent / tetrahydrofuran / 3 h

4: 79 percent / o-iodobenzoic acid; dimethyl sulfoxide / 2 h

5: 74 percent / Grubbs' 2-nd generation catalyst / CH₂Cl₂ / 2 h / Heating

6: 71 percent / dicyclohexylcarbodiimide / CH₂Cl₂ / 1 h / 20 °C

With hydrogenchloride; 2-Iodobenzoic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane;

DOI:10.1002/anie.200602569

Reference yield:

2-(4-methoxy-benzyl)-3-[4-(4-methoxy-benzyloxy)-butyl]-6-vinyl-[1,2]oxazinane-4-carboxylic acid methyl ester (916728-14-8) → (diethoxy-phosphoryl)-acetic acid 3-(4-methoxy-benzyl)-4-[4-(4-methoxy-benzyloxy)-butyl]-6-oxo-2-oxa-3-aza-bicyclo[3.3.1]non-7-en-5-yl ester (916728-21-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 80 percent / KHMDS; 3-phenyl-2-(p-toluenesulfonyl)-oxaziridine / tetrahydrofuran / 2.5 h / cooling

2: 97 percent / LiAlH₄ / diethyl ether; tetrahydrofuran / 2 h / cooling

3: p-toluenesulfonic acid / dimethylsulfoxide / 48 h / 20 °C

4: 93 percent / aq. HCl / tetrahydrofuran / 48 h

5: 64 percent / o-iodobenzoic acid; dimethyl sulfoxide / 2 h / 20 °C

6: 76 percent / tetrahydrofuran / 3 h

7: 79 percent / o-iodobenzoic acid; dimethyl sulfoxide / 2 h

8: 74 percent / Grubbs' 2-nd generation catalyst / CH₂Cl₂ / 2 h / Heating

9: 71 percent / dicyclohexylcarbodiimide / CH₂Cl₂ / 1 h / 20 °C

With hydrogenchloride; lithium aluminium tetrahydride; 2-Iodobenzoic acid; potassium hexamethylsilazane; toluene-4-sulfonic acid; dimethyl sulfoxide; 2-[(4-methylphenyl)sulfonyl]-3-phenyl-oxaziridine; dicyclohexyl-carbodiimide; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide;

DOI:10.1002/anie.200602569

upstream raw materials:

5-hydroxy-3-(4-methoxy-benzyl)-4-[4-(4-methoxy-benzyloxy)-butyl]-2-oxa-3-aza-bicyclo[3.3.1]non-7-en-6-one

diethylphosphonoacetic acid

2-(4-methoxy-benzyl)-3-[4-(4-methoxy-benzyloxy)-butyl]-6-vinyl-[1,2]oxazinane-4-carboxylic acid methyl ester

4-hydroxy-2-(4-methoxy-benzyl)-3-[4-(4-methoxy-benzyloxy)-butyl]-6-vinyl-[1,2]oxazinane-4-carbaldehyde

Downstream raw materials:

10-(4-methoxy-benzyl)-11-[4-(4-methoxy-benzyloxy)-butyl]-2,9-dioxa-10-aza-tricyclo[6.3.1.0^1,5]dodeca-4,6-dien-3-one