methyl (3S,5R)-3-(2-methoxy-2-oxoethyl)-2-(2,2,2-trifluoroacetyl)-5-[(S)-1-(2,4,6-triisopropylphenyl)ethoxy]isoxazolidine-3-carboxylate

Base Information

Chemical Name:methyl (3S,5R)-3-(2-methoxy-2-oxoethyl)-2-(2,2,2-trifluoroacetyl)-5-[(S)-1-(2,4,6-triisopropylphenyl)ethoxy]isoxazolidine-3-carboxylate
CAS No.:1611460-89-9
Molecular Formula:C₂₇H₃₈F₃NO₇
Molecular Weight:545.596
Hs Code.:

Synonyms:methyl (3S,5R)-3-(2-methoxy-2-oxoethyl)-2-(2,2,2-trifluoroacetyl)-5-[(S)-1-(2,4,6-triisopropylphenyl)ethoxy]isoxazolidine-3-carboxylate

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Chemical Property of methyl (3S,5R)-3-(2-methoxy-2-oxoethyl)-2-(2,2,2-trifluoroacetyl)-5-[(S)-1-(2,4,6-triisopropylphenyl)ethoxy]isoxazolidine-3-carboxylate

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Technology Process of methyl (3S,5R)-3-(2-methoxy-2-oxoethyl)-2-(2,2,2-trifluoroacetyl)-5-[(S)-1-(2,4,6-triisopropylphenyl)ethoxy]isoxazolidine-3-carboxylate

There total 5 articles about methyl (3S,5R)-3-(2-methoxy-2-oxoethyl)-2-(2,2,2-trifluoroacetyl)-5-[(S)-1-(2,4,6-triisopropylphenyl)ethoxy]isoxazolidine-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: 97.0%

: 1611460-84-4
methyl (3S,5R)-3-(2-methoxy-2-oxoethyl)-5-[(S)-1-(2,4,6-triisopropylphenyl)ethoxy]isoxazolidine-3-carboxylate

: 407-25-0
trifluoroacetic anhydride

: 1611460-89-9
methyl (3S,5R)-3-(2-methoxy-2-oxoethyl)-2-(2,2,2-trifluoroacetyl)-5-[(S)-1-(2,4,6-triisopropylphenyl)ethoxy]isoxazolidine-3-carboxylate

Guidance literature:: With triethylamine; In tetrahydrofuran; at 20 ℃;
DOI:10.1002/ejoc.201301739

Reference yield:

: 102225-88-7
(-)-(S)-1-(2,4,6-triisopropylphenyl)ethanol

: 1611460-89-9
methyl (3S,5R)-3-(2-methoxy-2-oxoethyl)-2-(2,2,2-trifluoroacetyl)-5-[(S)-1-(2,4,6-triisopropylphenyl)ethoxy]isoxazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: bis(1,5-cyclooctadiene)diiridium(I) dichloride; sodium carbonate / toluene / 24 h / 100 °C / Inert atmosphere

2: toluene / 48 h / 125 °C / Sealed tube; Inert atmosphere

3: formic acid; palladium 10% on activated carbon / methanol / 16 h / 20 °C / Inert atmosphere

4: triethylamine / tetrahydrofuran / 20 °C

With bis(1,5-cyclooctadiene)diiridium(I) dichloride; formic acid; palladium 10% on activated carbon; sodium carbonate; triethylamine; In tetrahydrofuran; methanol; toluene;
DOI:10.1002/ejoc.201301739

Reference yield:

: 860011-18-3
2-[(S)-1-((E)-1,2-Dichloro-vinyloxy)-ethyl]-1,3,5-triisopropyl-benzene

: 1611460-89-9
methyl (3S,5R)-3-(2-methoxy-2-oxoethyl)-2-(2,2,2-trifluoroacetyl)-5-[(S)-1-(2,4,6-triisopropylphenyl)ethoxy]isoxazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 - -40 °C

1.2: -40 - 20 °C / 760.05 Torr

2.1: toluene / 48 h / 125 °C / Sealed tube; Inert atmosphere

3.1: formic acid; palladium 10% on activated carbon / methanol / 16 h / 20 °C / Inert atmosphere

4.1: triethylamine / tetrahydrofuran / 20 °C

With n-butyllithium; formic acid; palladium 10% on activated carbon; triethylamine; In tetrahydrofuran; methanol; hexane; toluene;
DOI:10.1002/ejoc.201301739