5(S)-[1(R)-[(tert-butyldimethylsilyl)oxy]-2-phenylethyl]-3(R)-(cyclopropylmethyl)dihydrofuran-2(3H)-one

Base Information

• Chemical Name: 5(S)-[1(R)-[(tert-butyldimethylsilyl)oxy]-2-phenylethyl]-3(R)-(cyclopropylmethyl)dihydrofuran-2(3H)-one
• CAS No.: 155295-70-8
• Molecular Formula: C₂₂H₃₄O₃Si
• Molecular Weight: 374.596

Synonyms:5(S)-[1(R)-[(tert-butyldimethylsilyl)oxy]-2-phenylethyl]-3(R)-(cyclopropylmethyl)dihydrofuran-2(3H)-one

Chemical Property of 5(S)-[1(R)-[(tert-butyldimethylsilyl)oxy]-2-phenylethyl]-3(R)-(cyclopropylmethyl)dihydrofuran-2(3H)-one

Chemical Property:

Purity/Quality:

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Technology Process of 5(S)-[1(R)-[(tert-butyldimethylsilyl)oxy]-2-phenylethyl]-3(R)-(cyclopropylmethyl)dihydrofuran-2(3H)-one

There total 7 articles about 5(S)-[1(R)-[(tert-butyldimethylsilyl)oxy]-2-phenylethyl]-3(R)-(cyclopropylmethyl)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: 44.0%

t-butyldimethylsiyl triflate (69739-34-0) + (R)-3-Cyclopropylmethyl-5-(1-hydroxy-2-phenyl-ethyl)-dihydro-furan-2-one (220589-01-5) → 5(S)-[1(R)-[(tert-butyldimethylsilyl)oxy]-2-phenylethyl]-3(R)-(cyclopropylmethyl)dihydrofuran-2(3H)-one (155295-70-8) + 5(R)-[1(S)-[(tert-butyldimethylsilyl)oxy]-2-phenylethyl]-3(R)-(cyclopropylmethyl)dihydrofuran-2(3H)-one (155295-71-9)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 - 25 ℃; for 0.5h;

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(R)-[(tert-butyldimethylsilyl)oxy]-2-phenylethyl]-3(R)-(cyclopropylmethyl)dihydrofuran-2(3H)-one (155295-70-8)

Guidance literature:

Multi-step reaction with 5 steps

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

2.1: n-BuLi; i-Pr₂NH / hexane; tetrahydrofuran / 1 h / -78 °C

2.2: 56 percent / DMPU / hexane; tetrahydrofuran / 2.75 h / -78 - 0 °C

3.1: 92 percent / H₂O₂; LiOH*H₂O / tetrahydrofuran; H₂O / 19 h / 0 - 25 °C

4.1: 80 percent / MCPBA / CH₂Cl₂ / 15.25 h / 0 - 25 °C

5.1: 44 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 - 25 °C

With 2,6-dimethylpyridine; lithium hydroxide; sulfurous dibromide; n-butyllithium; 1,5-Hexadien; dihydrogen peroxide; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; hexane; dichloromethane; water; 1,2-dichloro-ethane; 1.1: Substitution / 2.1: Metallation / 2.2: Alkylation / 3.1: Hydrolysis / 4.1: Oxidation / 5.1: silylation;

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

Reference yield:

(E)-(4-bromobut-2-en-1-yl)benzene (40734-75-6) → 5(S)-[1(R)-[(tert-butyldimethylsilyl)oxy]-2-phenylethyl]-3(R)-(cyclopropylmethyl)dihydrofuran-2(3H)-one (155295-70-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-BuLi; i-Pr₂NH / hexane; tetrahydrofuran / 1 h / -78 °C

1.2: 56 percent / DMPU / hexane; tetrahydrofuran / 2.75 h / -78 - 0 °C

2.1: 92 percent / H₂O₂; LiOH*H₂O / tetrahydrofuran; H₂O / 19 h / 0 - 25 °C

3.1: 80 percent / MCPBA / CH₂Cl₂ / 15.25 h / 0 - 25 °C

4.1: 44 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 - 25 °C

With 2,6-dimethylpyridine; lithium hydroxide; n-butyllithium; dihydrogen peroxide; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; hexane; dichloromethane; water; 1.1: Metallation / 1.2: Alkylation / 2.1: Hydrolysis / 3.1: Oxidation / 4.1: silylation;

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

upstream raw materials:

t-butyldimethylsiyl triflate

(R)-3-Cyclopropylmethyl-5-(1-hydroxy-2-phenyl-ethyl)-dihydro-furan-2-one

1-phenyl-3-buten-2-ol

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

Downstream raw materials:

4(S),5(R)-bis[(tert-butyldimethylsilyl)oxy]-N-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-2(R)-(cyclopropylmethyl)-6-phenylhexanamide

(2R,4S,5R)-4,5-di(tert-butyldimethylsilyloxy)-2-(cyclopropylmethyl)-6-phenylhexanoic acid

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