Sch 58053 Benzyl Ether

Base Information

• Chemical Name: Sch 58053 Benzyl Ether
• CAS No.: 194367-71-0
• Molecular Formula: C₃₃H₂₉ClFNO₃
• Molecular Weight: 542.05
• DSSTox Substance ID: DTXSID80441290
• Nikkaji Number: J902.824B
• Mol file: 194367-71-0.mol

Synonyms:Sch 58053 Benzyl Ether;194367-71-0;(1R)-7-(4-chlorophenyl)-2-(4-fluorophenyl)-7-hydroxy-1-(4-phenylmethoxyphenyl)-2-azaspiro[3.5]nonan-3-one;DTXSID80441290;(3R)-7-Hydroxy-7-(4-chlorophenyl)-2-(4-fluorophenyl)-3-[4-(benzyloxy)phenyl]-2-azaspiro[3.5]nonan-1-one

Chemical Property of Sch 58053 Benzyl Ether

Chemical Property:

• Melting Point: 99-102°C
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 6.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 541.1819996
• Heavy Atom Count: 39
• Complexity: 817

Purity/Quality:

98% ^*data from raw suppliers

Sch58053BenzylEther ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(CCC12C(N(C2=O)C3=CC=C(C=C3)F)C4=CC=C(C=C4)OCC5=CC=CC=C5)(C6=CC=C(C=C6)Cl)O
• Isomeric SMILES: C1CC(CCC12[C@H](N(C2=O)C3=CC=C(C=C3)F)C4=CC=C(C=C4)OCC5=CC=CC=C5)(C6=CC=C(C=C6)Cl)O
• Uses: Protected Sch 58053 (S199950), an analog of Ezetimibe (E975000) Protected Sch 58053 (S199950), an analog of Ezetimibe (E975000).

Technology Process of Sch 58053 Benzyl Ether

There total 7 articles about Sch 58053 Benzyl Ether 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:

ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate (1489-97-0) → (R)-3-(4-Benzyloxy-phenyl)-7-(4-chloro-phenyl)-2-(4-fluoro-phenyl)-7-hydroxy-2-aza-spiro[3.5]nonan-1-one (194367-71-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) LDA / 1) THF, -20 deg C, 1 h, 2) THF, -20 deg C, 30 min, -20 deg C --> rt, 1 h

2: N-(2-naphthalenesulfonyl)-D-valine, BH₃*THF / various solvent(s) / 3 h / -78 °C

3: n-Bu₄NF / tetrahydrofuran / 1 h / Ambient temperature

4: 1.) Me₃Al / 1) CH₂Cl₂, toluene, rt, 30 min; 2) CH₂Cl₂, toluene. 50-55 deg C, 2 d

5: BnNEt₃Cl, (EtO)2P(O)Cl, aq. NaOH / CH₂Cl₂ / 2 h / Ambient temperature

6: toluene; various solvent(s) / 1.5 h / 48 - 52 °C / further solvents and temperatures

With sodium hydroxide; borane-THF; tetrabutyl ammonium fluoride; N-benzyl-N,N,N-triethylammonium chloride; trimethylaluminum; diethyl chlorophosphate; N-(2-naphthalenesulfonyl)-D-valine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/jo9704366

Reference yield:

ethyl 4-oxocyclohexane-1-carboxylate (17159-79-4) → (R)-3-(4-Benzyloxy-phenyl)-7-(4-chloro-phenyl)-2-(4-fluoro-phenyl)-7-hydroxy-2-aza-spiro[3.5]nonan-1-one (194367-71-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 81 percent / 4-MeC₆H₄SO₃H / Heating

2: 1.) LDA / 1) THF, -20 deg C, 1 h, 2) THF, -20 deg C, 30 min, -20 deg C --> rt, 1 h

3: N-(2-naphthalenesulfonyl)-D-valine, BH₃*THF / various solvent(s) / 3 h / -78 °C

4: n-Bu₄NF / tetrahydrofuran / 1 h / Ambient temperature

5: 1.) Me₃Al / 1) CH₂Cl₂, toluene, rt, 30 min; 2) CH₂Cl₂, toluene. 50-55 deg C, 2 d

6: BnNEt₃Cl, (EtO)2P(O)Cl, aq. NaOH / CH₂Cl₂ / 2 h / Ambient temperature

7: toluene; various solvent(s) / 1.5 h / 48 - 52 °C / further solvents and temperatures

With sodium hydroxide; borane-THF; tetrabutyl ammonium fluoride; N-benzyl-N,N,N-triethylammonium chloride; trimethylaluminum; diethyl chlorophosphate; toluene-4-sulfonic acid; N-(2-naphthalenesulfonyl)-D-valine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/jo9704366

Reference yield:

[(1,4-Dioxa-spiro[4.5]dec-8-ylidene)-ethoxy-methoxy]-trimethyl-silane (182227-16-3) → (R)-3-(4-Benzyloxy-phenyl)-7-(4-chloro-phenyl)-2-(4-fluoro-phenyl)-7-hydroxy-2-aza-spiro[3.5]nonan-1-one (194367-71-0)

Guidance literature:

Multi-step reaction with 5 steps

1: N-(2-naphthalenesulfonyl)-D-valine, BH₃*THF / various solvent(s) / 3 h / -78 °C

2: n-Bu₄NF / tetrahydrofuran / 1 h / Ambient temperature

3: 1.) Me₃Al / 1) CH₂Cl₂, toluene, rt, 30 min; 2) CH₂Cl₂, toluene. 50-55 deg C, 2 d

4: BnNEt₃Cl, (EtO)2P(O)Cl, aq. NaOH / CH₂Cl₂ / 2 h / Ambient temperature

5: toluene; various solvent(s) / 1.5 h / 48 - 52 °C / further solvents and temperatures

With sodium hydroxide; borane-THF; tetrabutyl ammonium fluoride; N-benzyl-N,N,N-triethylammonium chloride; trimethylaluminum; diethyl chlorophosphate; N-(2-naphthalenesulfonyl)-D-valine; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/jo9704366

upstream raw materials:

(4-chlorphenyl)magnesium bromide

(+)-(R)-2-(4-fluorophenyl)-3-(4-(benzyloxy)phenyl)-2-azaspiro[3.5]nonane-1,7-dione

ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate

ethyl 4-oxocyclohexane-1-carboxylate

Downstream raw materials:

(R)-7-(4-Chloro-phenyl)-2-(4-fluoro-phenyl)-7-hydroxy-3-(4-hydroxy-phenyl)-2-aza-spiro[3.5]nonan-1-one

Refernces