(1S,4R,5S)-ethyl 7-oxo-5-(m-tolyl)-6-oxabicyclo[3.2.0]heptane-4-carboxylate

Base Information

Chemical Name:(1S,4R,5S)-ethyl 7-oxo-5-(m-tolyl)-6-oxabicyclo[3.2.0]heptane-4-carboxylate
CAS No.:1399841-13-4
Molecular Formula:C₁₆H₁₈O₄
Molecular Weight:274.317
Hs Code.:

Synonyms:(1S,4R,5S)-ethyl 7-oxo-5-(m-tolyl)-6-oxabicyclo[3.2.0]heptane-4-carboxylate

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Chemical Property of (1S,4R,5S)-ethyl 7-oxo-5-(m-tolyl)-6-oxabicyclo[3.2.0]heptane-4-carboxylate

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Technology Process of (1S,4R,5S)-ethyl 7-oxo-5-(m-tolyl)-6-oxabicyclo[3.2.0]heptane-4-carboxylate

There total 3 articles about (1S,4R,5S)-ethyl 7-oxo-5-(m-tolyl)-6-oxabicyclo[3.2.0]heptane-4-carboxylate 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: 78.0%

: 1399840-96-0
(E)-ethyl 2-(3-methylbenzoyl)-6-oxohex-4-enoate

: ethyl 7-oxo-5-(m-tolyl)-6-oxabicyclo[3.2.0]heptane-4-carboxylate

: 1399841-13-4
(1S,4R,5S)-ethyl 7-oxo-5-(m-tolyl)-6-oxabicyclo[3.2.0]heptane-4-carboxylate

Guidance literature:: With (5aR,10bS)-2-(2,6-diethylphenyl)-4,5a,6,10b-tetrahydroindeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate; caesium carbonate; In dichloromethane; at 23 ℃; for 12h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;
DOI:10.1002/anie.201203382

Reference yield:

: 1399840-73-3
(E)-ethyl 2-(3-methylbenzoyl)-6-hydroxyhex-4-enoate

: ethyl 7-oxo-5-(m-tolyl)-6-oxabicyclo[3.2.0]heptane-4-carboxylate

: 1399841-13-4
(1S,4R,5S)-ethyl 7-oxo-5-(m-tolyl)-6-oxabicyclo[3.2.0]heptane-4-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: pyridinium chlorochromate / dichloromethane / 2 h / 23 °C / Inert atmosphere

2: (5aR,10bS)-2-(2,6-diethylphenyl)-4,5a,6,10b-tetrahydroindeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate; caesium carbonate / dichloromethane / 12 h / 23 °C / Inert atmosphere

With (5aR,10bS)-2-(2,6-diethylphenyl)-4,5a,6,10b-tetrahydroindeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate; caesium carbonate; pyridinium chlorochromate; In dichloromethane;
DOI:10.1002/anie.201203382

Reference yield:

: 33166-79-9
ethyl m-toluoylacetate

: ethyl 7-oxo-5-(m-tolyl)-6-oxabicyclo[3.2.0]heptane-4-carboxylate

: 1399841-13-4
(1S,4R,5S)-ethyl 7-oxo-5-(m-tolyl)-6-oxabicyclo[3.2.0]heptane-4-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 23 °C / Inert atmosphere

1.2: 23 °C / Inert atmosphere

2.1: pyridinium chlorochromate / dichloromethane / 2 h / 23 °C / Inert atmosphere

3.1: (5aR,10bS)-2-(2,6-diethylphenyl)-4,5a,6,10b-tetrahydroindeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate; caesium carbonate / dichloromethane / 12 h / 23 °C / Inert atmosphere

With (5aR,10bS)-2-(2,6-diethylphenyl)-4,5a,6,10b-tetrahydroindeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate; sodium hydride; caesium carbonate; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; mineral oil;
DOI:10.1002/anie.201203382