ethyl (5R-cis)- and (5R-trans)-5-benzyloxymethyl-5-(2,4-difluorophenyl)-2-oxo-3-tetrahydrofurancarboxylate

Base Information

Chemical Name:ethyl (5R-cis)- and (5R-trans)-5-benzyloxymethyl-5-(2,4-difluorophenyl)-2-oxo-3-tetrahydrofurancarboxylate
CAS No.:310882-04-3
Molecular Formula:C₂₁H₂₀F₂O₅
Molecular Weight:390.384
Hs Code.:

Synonyms:ethyl (5R-cis)- and (5R-trans)-5-benzyloxymethyl-5-(2,4-difluorophenyl)-2-oxo-3-tetrahydrofurancarboxylate

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Chemical Property of ethyl (5R-cis)- and (5R-trans)-5-benzyloxymethyl-5-(2,4-difluorophenyl)-2-oxo-3-tetrahydrofurancarboxylate

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Technology Process of ethyl (5R-cis)- and (5R-trans)-5-benzyloxymethyl-5-(2,4-difluorophenyl)-2-oxo-3-tetrahydrofurancarboxylate

There total 4 articles about ethyl (5R-cis)- and (5R-trans)-5-benzyloxymethyl-5-(2,4-difluorophenyl)-2-oxo-3-tetrahydrofurancarboxylate 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:

: 141113-37-3
(S)-(2-(2,4-difluorophenyl)oxiran-2-yl)methanol

: 310882-04-3
ethyl (5R-cis)- and (5R-trans)-5-benzyloxymethyl-5-(2,4-difluorophenyl)-2-oxo-3-tetrahydrofurancarboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 6.22 g / pyridinium p-toluenesulfonate / CH₂Cl₂ / 20 °C

2.1: NaH / tetrahydrofuran / 24 h / 50 - 60 °C

2.2: 6.36 g / p-toluenesulfonic acid monohydrate / methanol / 0.5 h / 20 °C

3.1: Et₃N / CH₂Cl₂ / 2 h / 20 °C

4.1: 5.15 g / NaH / dimethylformamide / 4 h / 20 °C

5.1: NaH; DMSO / 1 h / 20 °C

5.2: 85.9 percent / dimethylsulfoxide / 30 h / 75 - 80 °C

With pyridinium p-toluenesulfonate; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1.1: Addition / 2.1: Ring cleavage / 2.2: methanolysis / 3.1: mesylation / 4.1: Cyclization / 5.1: Metallation / 5.2: Ring cleavage;
DOI:10.1016/S0968-0896(00)00177-2

Reference yield:

: 310882-23-6
(2S)-2-(2,4-difluorophenyl)-2-[(tetrahydropyran-2-yloxy)methyl]oxirane

: 310882-04-3
ethyl (5R-cis)- and (5R-trans)-5-benzyloxymethyl-5-(2,4-difluorophenyl)-2-oxo-3-tetrahydrofurancarboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / tetrahydrofuran / 24 h / 50 - 60 °C

1.2: 6.36 g / p-toluenesulfonic acid monohydrate / methanol / 0.5 h / 20 °C

2.1: Et₃N / CH₂Cl₂ / 2 h / 20 °C

3.1: 5.15 g / NaH / dimethylformamide / 4 h / 20 °C

4.1: NaH; DMSO / 1 h / 20 °C

4.2: 85.9 percent / dimethylsulfoxide / 30 h / 75 - 80 °C

With sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1.1: Ring cleavage / 1.2: methanolysis / 2.1: mesylation / 3.1: Cyclization / 4.1: Metallation / 4.2: Ring cleavage;
DOI:10.1016/S0968-0896(00)00177-2

Reference yield:

: 310882-00-9
(2S)-3-benzyloxy-2-(2,4-difluorophenyl)-1,2-propanediol

: 310882-04-3
ethyl (5R-cis)- and (5R-trans)-5-benzyloxymethyl-5-(2,4-difluorophenyl)-2-oxo-3-tetrahydrofurancarboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: Et₃N / CH₂Cl₂ / 2 h / 20 °C

2.1: 5.15 g / NaH / dimethylformamide / 4 h / 20 °C

3.1: NaH; DMSO / 1 h / 20 °C

3.2: 85.9 percent / dimethylsulfoxide / 30 h / 75 - 80 °C

With sodium hydride; dimethyl sulfoxide; triethylamine; In dichloromethane; N,N-dimethyl-formamide; 1.1: mesylation / 2.1: Cyclization / 3.1: Metallation / 3.2: Ring cleavage;
DOI:10.1016/S0968-0896(00)00177-2