(4R,5S,7S)-7-hydroxy-8-formyl-4,9-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,8-diene

Base Information

• Chemical Name: (4R,5S,7S)-7-hydroxy-8-formyl-4,9-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,8-diene
• CAS No.: 1383736-63-7
• Molecular Formula: C₁₆H₁₇NO₃
• Molecular Weight: 271.316
• Mol file: 1383736-63-7.mol

Synonyms:(4R,5S,7S)-7-hydroxy-8-formyl-4,9-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,8-diene

Chemical Property of (4R,5S,7S)-7-hydroxy-8-formyl-4,9-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,8-diene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S,7S)-7-hydroxy-8-formyl-4,9-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,8-diene

There total 5 articles about (4R,5S,7S)-7-hydroxy-8-formyl-4,9-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,8-diene 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:

(4R,5S)-4,6-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,6-diene-7-carbaldehyde (1383736-55-7) → (4R,5S,7S)-7-hydroxy-8-formyl-4,9-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,8-diene (1383736-63-7) + (4R,5S,7R)-7-hydroxy-8-formyl-4,9-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,8-diene (1383736-62-6)

Guidance literature:

(4R,5S)-4,6-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,6-diene-7-carbaldehyde; With 2,2'-azobis(isobutyronitrile); bromine; potassium carbonate; In dichloromethane; at 40 ℃; Inert atmosphere;

With water; sodium acetate; In tetrahydrofuran; at 90 ℃; for 8h;

DOI:10.1021/ol301461e

Reference yield:

4-((4R,5R)-4-acetyl-5-methyl-2-phenyl-4,5-dihydrooxazol-4-yl)butanal (1383736-52-4) → (4R,5S,7S)-7-hydroxy-8-formyl-4,9-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,8-diene (1383736-63-7) + (4R,5S,7R)-7-hydroxy-8-formyl-4,9-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,8-diene (1383736-62-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: silica gel; N-ethyl-N,N-diisopropylamine / toluene / 48 h / 75 °C

2.1: 2,2'-azobis(isobutyronitrile); bromine; potassium carbonate / dichloromethane / 40 °C / Inert atmosphere

2.2: 8 h / 90 °C

With 2,2'-azobis(isobutyronitrile); bromine; silica gel; potassium carbonate; N-ethyl-N,N-diisopropylamine; In dichloromethane; toluene; 1.1: Aldol condensation;

DOI:10.1021/ol301461e

Reference yield:

(4R,5R)-methyl 5-methyl-4-(pent-4-en-1-yl)-2-phenyl-4,5-dihydrooxazole-4-carboxylate (1383736-53-5) → (4R,5S,7S)-7-hydroxy-8-formyl-4,9-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,8-diene (1383736-63-7) + (4R,5S,7R)-7-hydroxy-8-formyl-4,9-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,8-diene (1383736-62-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N,O-dimethylhydroxylamine*hydrochloride / tetrahydrofuran / 0.08 h / Inert atmosphere

1.2: -5 - 20 °C / Inert atmosphere

2.1: ozone / ethyl acetate / -78 °C

2.2: 8 h / Inert atmosphere; Reflux

3.1: silica gel; N-ethyl-N,N-diisopropylamine / toluene / 48 h / 75 °C

4.1: 2,2'-azobis(isobutyronitrile); bromine; potassium carbonate / dichloromethane / 40 °C / Inert atmosphere

4.2: 8 h / 90 °C

With 2,2'-azobis(isobutyronitrile); bromine; N,O-dimethylhydroxylamine*hydrochloride; silica gel; potassium carbonate; ozone; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene; 3.1: Aldol condensation;

DOI:10.1021/ol301461e

upstream raw materials:

4-((4R,5R)-4-acetyl-5-methyl-2-phenyl-4,5-dihydrooxazol-4-yl)butanal

(4R,5R)-methyl 5-methyl-4-(pent-4-en-1-yl)-2-phenyl-4,5-dihydrooxazole-4-carboxylate

1-((4R,5R)-5-methyl-4-(pent-4-en-1-yl)-2-phenyl-4,5-dihydrooxazol-4-yl)ethanone

(4R,5S)-4,6-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,6-diene-7-carbaldehyde