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

Base Information

• Chemical Name: 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
• CAS No.: 916728-22-8
• Molecular Formula: C₂₉H₃₃NO₆
• Molecular Weight: 491.584

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of 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

There total 10 articles about 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 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: 100.0%

(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) → 10-(4-methoxy-benzyl)-11-[4-(4-methoxy-benzyloxy)-butyl]-2,9-dioxa-10-aza-tricyclo[6.3.1.01,5]dodeca-4,6-dien-3-one (916728-22-8)

Guidance literature:

With 18-crown-6 ether; potassium carbonate; In toluene; for 2h;

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) → 10-(4-methoxy-benzyl)-11-[4-(4-methoxy-benzyloxy)-butyl]-2,9-dioxa-10-aza-tricyclo[6.3.1.01,5]dodeca-4,6-dien-3-one (916728-22-8)

Guidance literature:

Multi-step reaction with 7 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

7: 100 percent / potassium carbonate; 18-crown-6 ether / toluene / 2 h

With hydrogenchloride; 18-crown-6 ether; 2-Iodobenzoic acid; potassium carbonate; dimethyl sulfoxide; dicyclohexyl-carbodiimide; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; toluene;

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) → 10-(4-methoxy-benzyl)-11-[4-(4-methoxy-benzyloxy)-butyl]-2,9-dioxa-10-aza-tricyclo[6.3.1.01,5]dodeca-4,6-dien-3-one (916728-22-8)

Guidance literature:

Multi-step reaction with 10 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

10: 100 percent / potassium carbonate; 18-crown-6 ether / toluene / 2 h

With hydrogenchloride; lithium aluminium tetrahydride; 18-crown-6 ether; 2-Iodobenzoic acid; potassium hexamethylsilazane; potassium carbonate; 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; toluene;

DOI:10.1002/anie.200602569

upstream raw materials:

(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

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

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

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