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

Base Information

Chemical Name:(4R,5S,7R)-8-formyl-4,9-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,8-dien-7-yl benzoate
CAS No.:1383736-65-9
Molecular Formula:C₂₃H₂₁NO₄
Molecular Weight:375.424
Hs Code.:

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

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

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

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

: 532-32-1
sodium benzoate

: 1383736-55-7
(4R,5S)-4,6-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,6-diene-7-carbaldehyde

: 1383736-65-9
(4R,5S,7R)-8-formyl-4,9-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,8-dien-7-yl benzoate

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;

sodium benzoate; With water; potassium carbonate; In tetrahydrofuran; at 90 ℃; for 12h; optical yield given as %de; diastereoselective reaction;
DOI:10.1021/ol301461e

Reference yield:

: 1383736-52-4
4-((4R,5R)-4-acetyl-5-methyl-2-phenyl-4,5-dihydrooxazol-4-yl)butanal

: 1383736-65-9
(4R,5S,7R)-8-formyl-4,9-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,8-dien-7-yl benzoate

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: 12 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:

: 1383736-54-6
1-((4R,5R)-5-methyl-4-(pent-4-en-1-yl)-2-phenyl-4,5-dihydrooxazol-4-yl)ethanone

: 1383736-65-9
(4R,5S,7R)-8-formyl-4,9-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,8-dien-7-yl benzoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: ozone / ethyl acetate / -78 °C

1.2: 8 h / Inert atmosphere; Reflux

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

3.1: 2,2'-azobis(isobutyronitrile); bromine; potassium carbonate / dichloromethane / 40 °C / Inert atmosphere

3.2: 12 h / 90 °C

With 2,2'-azobis(isobutyronitrile); bromine; silica gel; potassium carbonate; ozone; N-ethyl-N,N-diisopropylamine; In dichloromethane; ethyl acetate; toluene; 2.1: Aldol condensation;
DOI:10.1021/ol301461e