Acetic acid (1R,2R,3R,7S)-1-hydroxymethyl-5-oxo-10-phenyl-4-oxa-tricyclo[4.3.1.0^3,7]dec-8-en-2-yl ester

Base Information

• Chemical Name: Acetic acid (1R,2R,3R,7S)-1-hydroxymethyl-5-oxo-10-phenyl-4-oxa-tricyclo[4.3.1.0^3,7]dec-8-en-2-yl ester
• CAS No.: 122594-59-6
• Molecular Formula: C₁₈H₁₈O₅
• Molecular Weight: 314.338

Synonyms:Acetic acid (1R,2R,3R,7S)-1-hydroxymethyl-5-oxo-10-phenyl-4-oxa-tricyclo[4.3.1.0^3,7]dec-8-en-2-yl ester

Chemical Property of Acetic acid (1R,2R,3R,7S)-1-hydroxymethyl-5-oxo-10-phenyl-4-oxa-tricyclo[4.3.1.0^3,7]dec-8-en-2-yl ester

Chemical Property:

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Technology Process of Acetic acid (1R,2R,3R,7S)-1-hydroxymethyl-5-oxo-10-phenyl-4-oxa-tricyclo[4.3.1.0^3,7]dec-8-en-2-yl ester

There total 3 articles about Acetic acid (1R,2R,3R,7S)-1-hydroxymethyl-5-oxo-10-phenyl-4-oxa-tricyclo[4.3.1.0^3,7]dec-8-en-2-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: 85.0%

Acetic acid (1S,2R,3R,7S)-1-formyl-5-oxo-10-phenyl-4-oxa-tricyclo[4.3.1.03,7]dec-8-en-2-yl ester (122594-60-9) → Acetic acid (1R,2R,3R,7S)-1-hydroxymethyl-5-oxo-10-phenyl-4-oxa-tricyclo[4.3.1.03,7]dec-8-en-2-yl ester (122594-59-6)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.333333h;

DOI:10.1021/jo00278a052

Reference yield:

(2R,3R)-2-acetoxy-1-(cinnamoyloxy)-3-vinylcyclohexa-3,5-diene (122594-51-8) → Acetic acid (1R,2R,3R,7S)-1-hydroxymethyl-5-oxo-10-phenyl-4-oxa-tricyclo[4.3.1.03,7]dec-8-en-2-yl ester (122594-59-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / benzene / 15 h / 110 °C

2: 1.) O₃, 2.) dimethyl sulfide (DMS) / 1.) CH₂Cl₂, -78 deg C, 3 min, 2.) from -78 deg C to RT, 2 h

3: 85 percent / NaBH₄ / methanol / 0.33 h / 0 °C

With sodium tetrahydroborate; dimethylsulfide; ozone; In methanol; benzene;

DOI:10.1021/jo00278a052

Reference yield:

(-)(1R,2R,5R,6R,7R,10S)-6-acetoxy-9-oxo-10-phenyl-5-vinyl-8-oxatricyclo<4.3.1.02,7>dec-3-ene (122594-52-9) → Acetic acid (1R,2R,3R,7S)-1-hydroxymethyl-5-oxo-10-phenyl-4-oxa-tricyclo[4.3.1.03,7]dec-8-en-2-yl ester (122594-59-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) O₃, 2.) dimethyl sulfide (DMS) / 1.) CH₂Cl₂, -78 deg C, 3 min, 2.) from -78 deg C to RT, 2 h

2: 85 percent / NaBH₄ / methanol / 0.33 h / 0 °C

With sodium tetrahydroborate; dimethylsulfide; ozone; In methanol;

DOI:10.1021/jo00278a052

upstream raw materials:

Acetic acid (1S,2R,3R,7S)-1-formyl-5-oxo-10-phenyl-4-oxa-tricyclo[4.3.1.0^3,7]dec-8-en-2-yl ester

(2R,3R)-2-acetoxy-1-(cinnamoyloxy)-3-vinylcyclohexa-3,5-diene

(-)(1R,2R,5R,6R,7R,10S)-6-acetoxy-9-oxo-10-phenyl-5-vinyl-8-oxatricyclo<4.3.1.0^2,7>dec-3-ene

Downstream raw materials:

(-)-(1R,2R,5R,6R,7R,10S)-6-acetoxy-5-<(benzoyloxy)methyl>-9-oxo-10-phenyl-8-oxatricyclo<4.3.1.0^2,7>dec-3-ene

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