5(S)-[1(S)-(benzoyloxy)-2-phenylethyl]-3(R)-[[1-(triphenylmethyl)-1H-imidazol-4-yl]methyl]dihydrofuran-2(3H)-one

Base Information

• Chemical Name: 5(S)-[1(S)-(benzoyloxy)-2-phenylethyl]-3(R)-[[1-(triphenylmethyl)-1H-imidazol-4-yl]methyl]dihydrofuran-2(3H)-one
• CAS No.: 220588-88-5
• Molecular Formula: C₄₂H₃₆N₂O₄
• Molecular Weight: 632.759

Synonyms:5(S)-[1(S)-(benzoyloxy)-2-phenylethyl]-3(R)-[[1-(triphenylmethyl)-1H-imidazol-4-yl]methyl]dihydrofuran-2(3H)-one

Chemical Property of 5(S)-[1(S)-(benzoyloxy)-2-phenylethyl]-3(R)-[[1-(triphenylmethyl)-1H-imidazol-4-yl]methyl]dihydrofuran-2(3H)-one

Chemical Property:

Purity/Quality:

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Technology Process of 5(S)-[1(S)-(benzoyloxy)-2-phenylethyl]-3(R)-[[1-(triphenylmethyl)-1H-imidazol-4-yl]methyl]dihydrofuran-2(3H)-one

There total 13 articles about 5(S)-[1(S)-(benzoyloxy)-2-phenylethyl]-3(R)-[[1-(triphenylmethyl)-1H-imidazol-4-yl]methyl]dihydrofuran-2(3H)-one 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: 34.0%

benzoyl chloride (98-88-4) + 5(RS)-[1(RS)-hydroxy-2-phenylethyl]-3(R)-[[1-(triphenylmethyl)-1H-imidazol-4-yl]methyl]dihydrofuran-2(3H)-one (220588-87-4) → 5(R)-[1(R)-(benzoyloxy)-2-phenylethyl]-3(R)-[[1-(triphenylmethyl)-1H-imidazol-4-yl]methyl]dihydrofuran-2(3H)-one + 5(S)-[1(S)-(benzoyloxy)-2-phenylethyl]-3(R)-[[1-(triphenylmethyl)-1H-imidazol-4-yl]methyl]dihydrofuran-2(3H)-one (220588-88-5)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 ℃; for 2.2h;

DOI:10.1016/S0968-0896(98)80011-4

Reference yield:

1-phenyl-3-buten-2-ol (6052-66-0,112370-40-8,123877-73-6) → 5(S)-[1(S)-(benzoyloxy)-2-phenylethyl]-3(R)-[[1-(triphenylmethyl)-1H-imidazol-4-yl]methyl]dihydrofuran-2(3H)-one (220588-88-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 1,5-hexadiene; SOBr₂ / 1,2-dichloro-ethane / 1.5 h / 0 °C

2.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

2.2: 48 percent / tetrahydrofuran / 3.5 h / -78 °C

3.1: NMMO*H₂O / OsO₄ / tetrahydrofuran; H₂O / 1 h / 25 °C

4.1: H₂O₂; LiOH*H₂O / tetrahydrofuran; H₂O / 0.75 h / 0 °C

5.1: 2.74 g / TFA / tetrahydrofuran / 3.75 h / 0 °C

6.1: 34 percent / Et₃N; DMAP / CH₂Cl₂ / 2.2 h / 0 °C

With dmap; lithium hydroxide; sulfurous dibromide; 1,5-Hexadien; NMMO*H₂O; dihydrogen peroxide; sodium hexamethyldisilazane; triethylamine; trifluoroacetic acid; osmium(VIII) oxide; In tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; 1.1: Substitution / 2.1: Metallation / 2.2: Evans' alkylation / 3.1: Oxidation / 4.1: Hydrolysis / 5.1: Cyclization / 6.1: Esterification;

DOI:10.1016/S0968-0896(98)80011-4

Reference yield:

(E)-(4-bromobut-2-en-1-yl)benzene (40734-75-6) → 5(S)-[1(S)-(benzoyloxy)-2-phenylethyl]-3(R)-[[1-(triphenylmethyl)-1H-imidazol-4-yl]methyl]dihydrofuran-2(3H)-one (220588-88-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

1.2: 48 percent / tetrahydrofuran / 3.5 h / -78 °C

2.1: NMMO*H₂O / OsO₄ / tetrahydrofuran; H₂O / 1 h / 25 °C

3.1: H₂O₂; LiOH*H₂O / tetrahydrofuran; H₂O / 0.75 h / 0 °C

4.1: 2.74 g / TFA / tetrahydrofuran / 3.75 h / 0 °C

5.1: 34 percent / Et₃N; DMAP / CH₂Cl₂ / 2.2 h / 0 °C

With dmap; lithium hydroxide; NMMO*H₂O; dihydrogen peroxide; sodium hexamethyldisilazane; triethylamine; trifluoroacetic acid; osmium(VIII) oxide; In tetrahydrofuran; dichloromethane; water; 1.1: Metallation / 1.2: Evans' alkylation / 2.1: Oxidation / 3.1: Hydrolysis / 4.1: Cyclization / 5.1: Esterification;

DOI:10.1016/S0968-0896(98)80011-4

upstream raw materials:

benzoyl chloride

5(RS)-[1(RS)-hydroxy-2-phenylethyl]-3(R)-[[1-(triphenylmethyl)-1H-imidazol-4-yl]methyl]dihydrofuran-2(3H)-one

1-phenyl-3-buten-2-ol

(E)-(4-bromobut-2-en-1-yl)benzene

Downstream raw materials:

4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-phenyl-2-(1-trityl-1H-imidazol-4-ylmethyl)-hexanoic acid

N-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-4(S),5(S)-dihydroxy-6-phenyl-2(R)-[[1-(triphenylmethyl)-1H-imidazol-4-yl]methyl]hexanamide

4(S),5(S)-bis[(tert-butyldimethylsilyl)oxy]-N-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-6-phenyl-2(R)-[[1-(triphenylmethyl)-1H-imidazol-4-yl]methyl]hexanamide

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