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

Base Information

• Chemical Name: 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
• CAS No.: 916728-20-6
• Molecular Formula: C₂₇H₃₃NO₆
• Molecular Weight: 467.562

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 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

There total 8 articles about 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 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: 74.0%

1-{4-hydroxy-2-(4-methoxy-benzyl)-3-[4-(4-methoxy-benzyloxy)-butyl]-6-vinyl-[1,2]oxazinan-4-yl}-propenone (916728-19-3) → 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)

Guidance literature:

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; for 2h; Heating;

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) → 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)

Guidance literature:

Multi-step reaction with 5 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

With hydrogenchloride; 2-Iodobenzoic acid; dimethyl sulfoxide; 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) → 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)

Guidance literature:

Multi-step reaction with 8 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

With hydrogenchloride; lithium aluminium tetrahydride; 2-Iodobenzoic acid; potassium hexamethylsilazane; toluene-4-sulfonic acid; dimethyl sulfoxide; 2-[(4-methylphenyl)sulfonyl]-3-phenyl-oxaziridine; 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:

1-{4-hydroxy-2-(4-methoxy-benzyl)-3-[4-(4-methoxy-benzyloxy)-butyl]-6-vinyl-[1,2]oxazinan-4-yl}-propenone

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

4-hydroxymethyl-2-(4-methoxy-benzyl)-3-[4-(4-methoxy-benzyloxy)-butyl]-6-vinyl-[1,2]oxazinan-4-ol

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

(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

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