(1'S,3R,6R)-3-[(4-benzyloxyphenyl)-(4-fluorophenylamino)-methyl]-6-(4-fluorophenyl)-tetrahydro-2H-pyran-2-one

Base Information

• Chemical Name: (1'S,3R,6R)-3-[(4-benzyloxyphenyl)-(4-fluorophenylamino)-methyl]-6-(4-fluorophenyl)-tetrahydro-2H-pyran-2-one
• CAS No.: 1416263-34-7
• Molecular Formula: C₃₁H₂₇F₂NO₃
• Molecular Weight: 499.557
• Mol file: 1416263-34-7.mol

Synonyms:(1'S,3R,6R)-3-[(4-benzyloxyphenyl)-(4-fluorophenylamino)-methyl]-6-(4-fluorophenyl)-tetrahydro-2H-pyran-2-one

Chemical Property of (1'S,3R,6R)-3-[(4-benzyloxyphenyl)-(4-fluorophenylamino)-methyl]-6-(4-fluorophenyl)-tetrahydro-2H-pyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1'S,3R,6R)-3-[(4-benzyloxyphenyl)-(4-fluorophenylamino)-methyl]-6-(4-fluorophenyl)-tetrahydro-2H-pyran-2-one

There total 29 articles about (1'S,3R,6R)-3-[(4-benzyloxyphenyl)-(4-fluorophenylamino)-methyl]-6-(4-fluorophenyl)-tetrahydro-2H-pyran-2-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: 68.0%

(1'R,6R)-3-[(4-benzyloxyphenyl)-(4-fluorophenylamino)-methyl]-6-(4-fluorophenyl)-5,6-dihydro-2H-pyran-2-one (1416263-33-6) → (1'S,3R,6R)-3-[(4-benzyloxyphenyl)-(4-fluorophenylamino)-methyl]-6-(4-fluorophenyl)-tetrahydro-2H-pyran-2-one (1416263-34-7) + C31H29F2NO3 (1445455-04-8)

Guidance literature:

With L-Selectride; In tetrahydrofuran; at -78 ℃; for 2h;

DOI:10.1021/jo400807c

Reference yield:

(2R)-2-(4-fluorophenyl)-3,4-dihydro-2H-pyran-4-ol (1416263-27-8) → (1'S,3R,6R)-3-[(4-benzyloxyphenyl)-(4-fluorophenylamino)-methyl]-6-(4-fluorophenyl)-tetrahydro-2H-pyran-2-one (1416263-34-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: dihydrogen peroxide; molybdenum(VI) oxide / acetonitrile / 24 h

2.1: pyridine; acetic anhydride / dichloromethane / 2 h / 20 °C

3.1: toluene / 72 h / Reflux

4.1: potassium iodide; chloro-trimethyl-silane / acetonitrile / 0.58 h / 20 °C

5.1: chloro-trimethyl-silane; 1H-imidazole / dichloromethane / 0.5 h / 20 °C

5.2: 0.25 h / 20 °C

6.1: lithium hydroxide / tetrahydrofuran; water / 18 h

7.1: triphenylphosphine; di-isopropyl azodicarboxylate / 3 h / 0 °C

With pyridine; 1H-imidazole; chloro-trimethyl-silane; di-isopropyl azodicarboxylate; dihydrogen peroxide; acetic anhydride; triphenylphosphine; potassium iodide; molybdenum(VI) oxide; lithium hydroxide; In tetrahydrofuran; dichloromethane; water; toluene; acetonitrile; 7.1: |Mitsunobu Displacement;

DOI:10.1021/jo400807c

Reference yield:

4-Fluoronitrobenzene (350-46-9,178603-76-4) → (1'S,3R,6R)-3-[(4-benzyloxyphenyl)-(4-fluorophenylamino)-methyl]-6-(4-fluorophenyl)-tetrahydro-2H-pyran-2-one (1416263-34-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: zinc; ammonium chloride / water / 0.25 h / 60 °C

2.1: methanesulfonic acid / acetone / 2 h / 20 °C

3.1: toluene / 72 h / Reflux

4.1: potassium iodide; chloro-trimethyl-silane / acetonitrile / 0.58 h / 20 °C

5.1: chloro-trimethyl-silane; 1H-imidazole / dichloromethane / 0.5 h / 20 °C

5.2: 0.25 h / 20 °C

6.1: lithium hydroxide / tetrahydrofuran; water / 18 h

7.1: triphenylphosphine; di-isopropyl azodicarboxylate / 3 h / 0 °C

With 1H-imidazole; chloro-trimethyl-silane; methanesulfonic acid; di-isopropyl azodicarboxylate; ammonium chloride; triphenylphosphine; potassium iodide; lithium hydroxide; zinc; In tetrahydrofuran; dichloromethane; water; acetone; toluene; acetonitrile; 7.1: |Mitsunobu Displacement;

DOI:10.1021/jo400807c

upstream raw materials:

(1'R,6R)-3-[(4-benzyloxyphenyl)-(4-fluorophenylamino)-methyl]-6-(4-fluorophenyl)-5,6-dihydro-2H-pyran-2-one

4-fluorobenzaldehyde

(2R)-2-(4-fluorophenyl)-3,4-dihydro-2H-pyran-4-ol

4-hydroxy-benzaldehyde

Downstream raw materials:

(3R,4S,3'R)-1-(4-fluorophenyl)-4-(4-hydroxyphenyl)-3-[3'-(4-fluorophenyl)-3'-hydroxy-propyl]-azetidin-2-one