Acetic acid (3aR,5R,6S,7aR)-5-acetoxymethyl-1-(4-methoxy-phenyl)-2-oxo-hexahydro-pyrano[3,2-d]oxazol-6-yl ester

Base Information

• Chemical Name: Acetic acid (3aR,5R,6S,7aR)-5-acetoxymethyl-1-(4-methoxy-phenyl)-2-oxo-hexahydro-pyrano[3,2-d]oxazol-6-yl ester
• CAS No.: 413193-43-8
• Molecular Formula: C₁₈H₂₁NO₈
• Molecular Weight: 379.367

Synonyms:Acetic acid (3aR,5R,6S,7aR)-5-acetoxymethyl-1-(4-methoxy-phenyl)-2-oxo-hexahydro-pyrano[3,2-d]oxazol-6-yl ester

Chemical Property of Acetic acid (3aR,5R,6S,7aR)-5-acetoxymethyl-1-(4-methoxy-phenyl)-2-oxo-hexahydro-pyrano[3,2-d]oxazol-6-yl ester

Chemical Property:

Purity/Quality:

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Technology Process of Acetic acid (3aR,5R,6S,7aR)-5-acetoxymethyl-1-(4-methoxy-phenyl)-2-oxo-hexahydro-pyrano[3,2-d]oxazol-6-yl ester

There total 4 articles about Acetic acid (3aR,5R,6S,7aR)-5-acetoxymethyl-1-(4-methoxy-phenyl)-2-oxo-hexahydro-pyrano[3,2-d]oxazol-6-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: 82.0%

Acetic acid (2R,3S,6R)-2-acetoxymethyl-6-(4-methoxy-phenylcarbamoyloxy)-3,6-dihydro-2H-pyran-3-yl ester (413192-48-0) → Acetic acid (3aR,5R,6S,7aR)-5-acetoxymethyl-1-(4-methoxy-phenyl)-2-oxo-hexahydro-pyrano[3,2-d]oxazol-6-yl ester (413193-43-8)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dimethyl sulfoxide; at 90 ℃; for 24h;

DOI:10.1021/ja012126h

Reference yield:

((2R,3S)-3-acetoxy-6-hydroxy-3,6-dihydro-2H-pyran-2-yl)methyl acetate (92131-90-3) → Acetic acid (3aR,5R,6S,7aR)-5-acetoxymethyl-1-(4-methoxy-phenyl)-2-oxo-hexahydro-pyrano[3,2-d]oxazol-6-yl ester (413193-43-8)

Guidance literature:

Multi-step reaction with 2 steps

1: DBU / CH₂Cl₂ / 1 h / 25 °C

2: 82 percent / o-iodoxybenzoic acid / tetrahydrofuran; dimethylsulfoxide / 24 h / 90 °C

With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/ja012126h

Reference yield:

4-Methoxyphenyl isocyanate (5416-93-3) → Acetic acid (3aR,5R,6S,7aR)-5-acetoxymethyl-1-(4-methoxy-phenyl)-2-oxo-hexahydro-pyrano[3,2-d]oxazol-6-yl ester (413193-43-8)

Guidance literature:

Multi-step reaction with 2 steps

1: DBU / CH₂Cl₂ / 1 h / 25 °C

2: 82 percent / o-iodoxybenzoic acid / tetrahydrofuran; dimethylsulfoxide / 24 h / 90 °C

With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/ja012126h

upstream raw materials:

Acetic acid (2R,3S,6R)-2-acetoxymethyl-6-(4-methoxy-phenylcarbamoyloxy)-3,6-dihydro-2H-pyran-3-yl ester

((2R,3S)-3-acetoxy-6-hydroxy-3,6-dihydro-2H-pyran-2-yl)methyl acetate

4-Methoxyphenyl isocyanate

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