(2R-cis)-2-benzyloxymethyl-4-cyanomethyl-2-(2,4-difluorophenyl)tetrahydrofuran

Base Information

Chemical Name:(2R-cis)-2-benzyloxymethyl-4-cyanomethyl-2-(2,4-difluorophenyl)tetrahydrofuran
CAS No.:310882-11-2
Molecular Formula:C₂₀H₁₉F₂NO₂
Molecular Weight:343.373
Hs Code.:

Synonyms:(2R-cis)-2-benzyloxymethyl-4-cyanomethyl-2-(2,4-difluorophenyl)tetrahydrofuran

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Chemical Property of (2R-cis)-2-benzyloxymethyl-4-cyanomethyl-2-(2,4-difluorophenyl)tetrahydrofuran

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Technology Process of (2R-cis)-2-benzyloxymethyl-4-cyanomethyl-2-(2,4-difluorophenyl)tetrahydrofuran

There total 9 articles about (2R-cis)-2-benzyloxymethyl-4-cyanomethyl-2-(2,4-difluorophenyl)tetrahydrofuran 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: 88.8%

: 151-50-8
potassium cyanide

: 310882-08-7
(2R-cis)-2-benzyloxymethyl-2-(2,4-difluorophenyl)-4-[[(4-methylphenyl)sulfonyloxy]methyl]tetrahydrofuran

: 310882-11-2
(2R-cis)-2-benzyloxymethyl-4-cyanomethyl-2-(2,4-difluorophenyl)tetrahydrofuran

Guidance literature:: In dimethyl sulfoxide; at 55 ℃; for 15h;
DOI:10.1016/S0968-0896(00)00177-2

Reference yield:

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

: 310882-11-2
(2R-cis)-2-benzyloxymethyl-4-cyanomethyl-2-(2,4-difluorophenyl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 9 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

6.1: 94.8 percent / NaBH₄; LiCl / ethanol / 28 h / 20 °C

7.1: 4-(dimethylamino)pyridine; Et₃N / CH₂Cl₂ / 15.5 h / 20 °C

8.1: 1.50 g / NaH / toluene / 4 h / Heating

9.1: 88.8 percent / dimethylsulfoxide / 15 h / 55 °C

With dmap; sodium tetrahydroborate; pyridinium p-toluenesulfonate; sodium hydride; dimethyl sulfoxide; triethylamine; lithium chloride; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 1.1: Addition / 2.1: Ring cleavage / 2.2: methanolysis / 3.1: mesylation / 4.1: Cyclization / 5.1: Metallation / 5.2: Ring cleavage / 6.1: Reduction / 7.1: Tosylation / 8.1: Cyclization / 9.1: Substitution;
DOI:10.1016/S0968-0896(00)00177-2

Reference yield:

: (2R)-benzyloxymethyl-2-(2,4-difluorophenyl)oxirane

: 310882-11-2
(2R-cis)-2-benzyloxymethyl-4-cyanomethyl-2-(2,4-difluorophenyl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaH; DMSO / 1 h / 20 °C

1.2: 85.9 percent / dimethylsulfoxide / 30 h / 75 - 80 °C

2.1: 94.8 percent / NaBH₄; LiCl / ethanol / 28 h / 20 °C

3.1: 4-(dimethylamino)pyridine; Et₃N / CH₂Cl₂ / 15.5 h / 20 °C

4.1: 1.50 g / NaH / toluene / 4 h / Heating

5.1: 88.8 percent / dimethylsulfoxide / 15 h / 55 °C

With dmap; sodium tetrahydroborate; sodium hydride; dimethyl sulfoxide; triethylamine; lithium chloride; In ethanol; dichloromethane; dimethyl sulfoxide; toluene; 1.1: Metallation / 1.2: Ring cleavage / 2.1: Reduction / 3.1: Tosylation / 4.1: Cyclization / 5.1: Substitution;
DOI:10.1016/S0968-0896(00)00177-2