tert-butyl 4-[1-hydroxy-3-(4-methoxyphenyl)-(1S,2E)-2-propenyl]-2,2-dimethyl-(4R)-1,3-oxazolane-3-carboxylate

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Chemical Name:tert-butyl 4-[1-hydroxy-3-(4-methoxyphenyl)-(1S,2E)-2-propenyl]-2,2-dimethyl-(4R)-1,3-oxazolane-3-carboxylate
CAS No.:906478-65-7
Molecular Formula:C₂₀H₂₉NO₅
Molecular Weight:363.454
Hs Code.:

Synonyms:tert-butyl 4-[1-hydroxy-3-(4-methoxyphenyl)-(1S,2E)-2-propenyl]-2,2-dimethyl-(4R)-1,3-oxazolane-3-carboxylate

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Chemical Property of tert-butyl 4-[1-hydroxy-3-(4-methoxyphenyl)-(1S,2E)-2-propenyl]-2,2-dimethyl-(4R)-1,3-oxazolane-3-carboxylate

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Technology Process of tert-butyl 4-[1-hydroxy-3-(4-methoxyphenyl)-(1S,2E)-2-propenyl]-2,2-dimethyl-(4R)-1,3-oxazolane-3-carboxylate

There total 4 articles about tert-butyl 4-[1-hydroxy-3-(4-methoxyphenyl)-(1S,2E)-2-propenyl]-2,2-dimethyl-(4R)-1,3-oxazolane-3-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: 89.0%

: 906478-63-5
tert-butyl 4-[1-hydroxy-3-(4-methoxyphenyl)-(1S)-2-propynyl]-2,2-dimethyl-(4R)-1,3-oxazolane-3-carboxylate

: 906478-65-7
tert-butyl 4-[1-hydroxy-3-(4-methoxyphenyl)-(1S,2E)-2-propenyl]-2,2-dimethyl-(4R)-1,3-oxazolane-3-carboxylate

Guidance literature:: With sodium bis(2-methoxyethoxy)aluminium dihydride; In diethyl ether; toluene; at 0 ℃; for 1h;
DOI:10.1016/j.tetasy.2006.05.007

Reference yield:

: 60512-57-4
1-(2,2-dibromovinyl)-4-methoxybenzene

: 906478-65-7
tert-butyl 4-[1-hydroxy-3-(4-methoxyphenyl)-(1S,2E)-2-propenyl]-2,2-dimethyl-(4R)-1,3-oxazolane-3-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 1.45 g / n-BuLi / tetrahydrofuran; hexane / -78 - 30 °C

2.1: n-BuLi / tetrahydrofuran; hexane / -78 - 30 °C

2.2: 87 percent / tetrahydrofuran; hexane / 3 h / -78 °C

3.1: 89 percent / sodium bis-(2-methoxyethoxy)-aluminium hydride / toluene; diethyl ether / 1 h / 0 °C

With n-butyllithium; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; diethyl ether; hexane; toluene;
DOI:10.1016/j.tetasy.2006.05.007

Reference yield:

: 123-11-5
4-methoxy-benzaldehyde

: 906478-65-7
tert-butyl 4-[1-hydroxy-3-(4-methoxyphenyl)-(1S,2E)-2-propenyl]-2,2-dimethyl-(4R)-1,3-oxazolane-3-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: PPh₃; triethylamine / CH₂Cl₂ / 30 h / -30 °C

1.2: 4.0 g / CH₂Cl₂ / 3 h / -30 - 30 °C

2.1: 1.45 g / n-BuLi / tetrahydrofuran; hexane / -78 - 30 °C

3.1: n-BuLi / tetrahydrofuran; hexane / -78 - 30 °C

3.2: 87 percent / tetrahydrofuran; hexane / 3 h / -78 °C

4.1: 89 percent / sodium bis-(2-methoxyethoxy)-aluminium hydride / toluene; diethyl ether / 1 h / 0 °C

With n-butyllithium; triethylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene;
DOI:10.1016/j.tetasy.2006.05.007