2-((2S,4R,5R)-2-((tert-butyldimethylsilyloxy)methyl)-5-(2-hydroxyethyl)-1-(2,2,2-trifluoroacetyl)piperidin-4-yl)ethyl benzoate

Base Information

• Chemical Name: 2-((2S,4R,5R)-2-((tert-butyldimethylsilyloxy)methyl)-5-(2-hydroxyethyl)-1-(2,2,2-trifluoroacetyl)piperidin-4-yl)ethyl benzoate
• CAS No.: 1365034-52-1
• Molecular Formula: C₂₅H₃₈F₃NO₅Si
• Molecular Weight: 517.661
• Mol file: 1365034-52-1.mol

Synonyms:

Chemical Property of 2-((2S,4R,5R)-2-((tert-butyldimethylsilyloxy)methyl)-5-(2-hydroxyethyl)-1-(2,2,2-trifluoroacetyl)piperidin-4-yl)ethyl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((2S,4R,5R)-2-((tert-butyldimethylsilyloxy)methyl)-5-(2-hydroxyethyl)-1-(2,2,2-trifluoroacetyl)piperidin-4-yl)ethyl benzoate

There total 32 articles about 2-((2S,4R,5R)-2-((tert-butyldimethylsilyloxy)methyl)-5-(2-hydroxyethyl)-1-(2,2,2-trifluoroacetyl)piperidin-4-yl)ethyl benzoate 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: 29.0%

1-((2S,4R,5R)-2-((tert-butyldimethylsilyloxy)methyl)-4,5-bis(2-hydroxyethyl)-piperidin-1-yl)-2,2,2-trifluoroethanone (1312224-57-9) + benzoic acid anhydride (93-97-0) → 2-((2S,4R,5R)-2-((tert-butyldimethylsilyloxy)methyl)-5-(2-hydroxyethyl)-1-(2,2,2-trifluoroacetyl)piperidin-4-yl)ethyl benzoate (1365034-52-1) + 2-((3R,4R,6S)-6-((tert-butyldimethylsilyloxy)methyl)-4-(2-hydroxyethyl)-1-(2,2,2-trifluoroacetyl)piperidin-3-yl)ethyl benzoate (1365034-53-2)

Guidance literature:

1-((2S,4R,5R)-2-((tert-butyldimethylsilyloxy)methyl)-4,5-bis(2-hydroxyethyl)-piperidin-1-yl)-2,2,2-trifluoroethanone; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

benzoic acid anhydride; In tetrahydrofuran; at -78 - 20 ℃; regioselective reaction; Inert atmosphere;

DOI:10.1021/jo2026349

Reference yield:

((1R,2R,4R,5R)-4,5-bis(benzyloxy)-2-((tert-butyldimethylsilyloxy)methyl)cyclohexyl)methanol (956006-05-6) → 2-((2S,4R,5R)-2-((tert-butyldimethylsilyloxy)methyl)-5-(2-hydroxyethyl)-1-(2,2,2-trifluoroacetyl)piperidin-4-yl)ethyl benzoate (1365034-52-1) + 2-((3R,4R,6S)-6-((tert-butyldimethylsilyloxy)methyl)-4-(2-hydroxyethyl)-1-(2,2,2-trifluoroacetyl)piperidin-3-yl)ethyl benzoate (1365034-53-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 1H-imidazole; iodine; triphenylphosphine / tetrahydrofuran / 0.42 h / Inert atmosphere

2.1: camphorsulfonic acid / methanol / 4 h / 20 °C / Inert atmosphere

3.1: indium(III) chloride / acetonitrile; benzene / 0.67 h / 20 °C / Inert atmosphere

3.2: Inert atmosphere; Irradiation

4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

4.2: -78 °C / Inert atmosphere

5.1: samarium diiodide / tetrahydrofuran; methanol / Inert atmosphere

5.2: air

6.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

7.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 48 h / Inert atmosphere

8.1: gel supported NaIO₄ / dichloromethane / Inert atmosphere

9.1: sodium tetrahydroborate / methanol / 1 h / 0 °C / Inert atmosphere

10.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

10.2: -78 - 20 °C / Inert atmosphere

With 1H-imidazole; indium(III) chloride; sodium tetrahydroborate; n-butyllithium; samarium diiodide; di-isopropyl azodicarboxylate; palladium 10% on activated carbon; hydrogen; iodine; triphenylphosphine; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; acetonitrile; benzene;

DOI:10.1021/jo2026349

Reference yield:

((1R,2R,4R,5R)-4,5-bis(benzyloxy)-2-(iodomethyl)cyclohexylmethoxy)(tert-butyl)dimethylsilane (956006-37-4) → 2-((2S,4R,5R)-2-((tert-butyldimethylsilyloxy)methyl)-5-(2-hydroxyethyl)-1-(2,2,2-trifluoroacetyl)piperidin-4-yl)ethyl benzoate (1365034-52-1) + 2-((3R,4R,6S)-6-((tert-butyldimethylsilyloxy)methyl)-4-(2-hydroxyethyl)-1-(2,2,2-trifluoroacetyl)piperidin-3-yl)ethyl benzoate (1365034-53-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: camphorsulfonic acid / methanol / 4 h / 20 °C / Inert atmosphere

2.1: indium(III) chloride / acetonitrile; benzene / 0.67 h / 20 °C / Inert atmosphere

2.2: Inert atmosphere; Irradiation

3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

3.2: -78 °C / Inert atmosphere

4.1: samarium diiodide / tetrahydrofuran; methanol / Inert atmosphere

4.2: air

5.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

6.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 48 h / Inert atmosphere

7.1: gel supported NaIO₄ / dichloromethane / Inert atmosphere

8.1: sodium tetrahydroborate / methanol / 1 h / 0 °C / Inert atmosphere

9.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

9.2: -78 - 20 °C / Inert atmosphere

With indium(III) chloride; sodium tetrahydroborate; n-butyllithium; samarium diiodide; di-isopropyl azodicarboxylate; palladium 10% on activated carbon; hydrogen; triphenylphosphine; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; acetonitrile; benzene;

DOI:10.1021/jo2026349

upstream raw materials:

(S,E)-4-benzyl-3-(2-(tert-butyldimethylsilyloxy)ethylideneamino)oxazolidin-2-one

(1S,3R,4R,6R)-3-((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl) 4-((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl) 7-oxabicyclo[4.1.0]heptane-3,4-dicarboxylate

(1R,2R,4R,5R)-bis((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl) 4-(benzyloxy)-5-hydroxycyclohexane-1,2-dicarboxylate

(1R,2R,4R,5R)-bis((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl) 4,5-bis(benzyloxy)cyclohexane-1,2-dicarboxylate