(4S,5S)-3-(tert-butoxycarbonyl)-2-(4-methoxyphenyl)-4-<(E)-1-propenyl>-1,3-oxazolane-5-carboxylic acid

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Chemical Name:(4S,5S)-3-(tert-butoxycarbonyl)-2-(4-methoxyphenyl)-4-<(E)-1-propenyl>-1,3-oxazolane-5-carboxylic acid
CAS No.:220652-56-2
Molecular Formula:C₁₉H₂₅NO₆
Molecular Weight:363.411
Hs Code.:

Synonyms:(4S,5S)-3-(tert-butoxycarbonyl)-2-(4-methoxyphenyl)-4-<(E)-1-propenyl>-1,3-oxazolane-5-carboxylic acid

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Chemical Property of (4S,5S)-3-(tert-butoxycarbonyl)-2-(4-methoxyphenyl)-4-<(E)-1-propenyl>-1,3-oxazolane-5-carboxylic acid

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Technology Process of (4S,5S)-3-(tert-butoxycarbonyl)-2-(4-methoxyphenyl)-4-<(E)-1-propenyl>-1,3-oxazolane-5-carboxylic acid

There total 8 articles about (4S,5S)-3-(tert-butoxycarbonyl)-2-(4-methoxyphenyl)-4-<(E)-1-propenyl>-1,3-oxazolane-5-carboxylic acid 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: 95.0%

: 220652-55-1
3-(tert-butyl) 5-methyl (4S,5S)-2-(4-methoxyphenyl)-4-<(E)-1-propenyl>-1,3-oxazolane-3,5-dicarboxylate

: 220652-56-2
(4S,5S)-3-(tert-butoxycarbonyl)-2-(4-methoxyphenyl)-4-<(E)-1-propenyl>-1,3-oxazolane-5-carboxylic acid

Guidance literature:: With lithium hydroxide; In methanol; water; for 0.5h; Ambient temperature;
DOI:10.1016/S0040-4020(98)01051-5

Reference yield:

: 81838-85-9
tert-butyl (2E,4E)-2,4-hexadienoate

: 220652-56-2
(4S,5S)-3-(tert-butoxycarbonyl)-2-(4-methoxyphenyl)-4-<(E)-1-propenyl>-1,3-oxazolane-5-carboxylic acid

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) n-BuLi, 3.) (+)-(camphorsulfonyloxaziridine / 1.) hexane, -78 deg C, 1 h, 2.) THF, -78 deg C, 1 h, 3.) -78 deg C, 6 h; warm to room temperature

2: 93 percent / Pd(PPh₃)4, N,N'-dimethylbarbituric acid / CH₂Cl₂ / Ambient temperature

3: 201 g / Et₃N / tetrahydrofuran / 1.) room temperature, 1 h, 2.) reflux, overnight

4: 98 percent formic acid / 3 h / 60 °C

5: SOCl₂, Et₃N / 2.5 h / Heating

6: Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

7: NaOMe / methanol / 0.75 h / 0 °C

8: 95 percent / pyridinium p-toluenesulfonate / toluene / 4 h / 80 °C

9: 95 percent / LiOH / methanol; H₂O / 0.5 h / Ambient temperature

With dmap; lithium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; formic acid; thionyl chloride; 1,3-dimethylbarbituric acid; sodium methylate; pyridinium p-toluenesulfonate; (1S)-(+)-(10-camphorsulfonyl)-oxaziridine; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; toluene;
DOI:10.1016/S0040-4020(98)01051-5

Reference yield:

: 198543-54-3
tert-butyl (2S,3S,4E)-3-allyl<(1R)-1-phenylethyl>amino-2-hydroxy-4-hexenoate

: 220652-56-2
(4S,5S)-3-(tert-butoxycarbonyl)-2-(4-methoxyphenyl)-4-<(E)-1-propenyl>-1,3-oxazolane-5-carboxylic acid

Guidance literature:: Multi-step reaction with 8 steps

1: 93 percent / Pd(PPh₃)4, N,N'-dimethylbarbituric acid / CH₂Cl₂ / Ambient temperature

2: 201 g / Et₃N / tetrahydrofuran / 1.) room temperature, 1 h, 2.) reflux, overnight

3: 98 percent formic acid / 3 h / 60 °C

4: SOCl₂, Et₃N / 2.5 h / Heating

5: Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

6: NaOMe / methanol / 0.75 h / 0 °C

7: 95 percent / pyridinium p-toluenesulfonate / toluene / 4 h / 80 °C

8: 95 percent / LiOH / methanol; H₂O / 0.5 h / Ambient temperature

With dmap; lithium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; formic acid; thionyl chloride; 1,3-dimethylbarbituric acid; sodium methylate; pyridinium p-toluenesulfonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; toluene;
DOI:10.1016/S0040-4020(98)01051-5