4-Methoxy-5-[(Z)-methoxy[(2S,3R)-3-phenyloxiranyl]methylene]-2(5H)-furanone

Base Information

• Chemical Name: 4-Methoxy-5-[(Z)-methoxy[(2S,3R)-3-phenyloxiranyl]methylene]-2(5H)-furanone
• CAS No.: 40072-82-0
• Molecular Formula: C₁₅H₁₄O₅
• Molecular Weight: 274.273
• Mol file: 40072-82-0.mol

Synonyms:

Chemical Property of 4-Methoxy-5-[(Z)-methoxy[(2S,3R)-3-phenyloxiranyl]methylene]-2(5H)-furanone

Chemical Property:

• PSA: 57.29000
• LogP: 2.07160

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-Methoxy-5-[(Z)-methoxy[(2S,3R)-3-phenyloxiranyl]methylene]-2(5H)-furanone

There total 35 articles about 4-Methoxy-5-[(Z)-methoxy[(2S,3R)-3-phenyloxiranyl]methylene]-2(5H)-furanone 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:

4-methoxy-5H-furan-2-one (69556-70-3) → 4-Methoxy-5-[1-methoxy-1-((2S,3R)-3-phenyl-oxiranyl)-meth-(Z)-ylidene]-5H-furan-2-one (40072-82-0,67921-19-1,109009-80-5,109009-81-6,111767-57-8,111767-58-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 5.7 g / n-butyl-lithium, diisopropylamide / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 0.33 h / -78 °C

2: 94 percent / tetrahydrofuran / -78 deg C, 1 h, 20 deg C, 1 h

3: 1.) BF₃*Et₂O / 1.)diethyl ether, -78 deg C, 2 h, 2.) -78 deg C, 1 h, RT_., 16 h

4: 85 percent / H₂ / Lindlar cat. / tetrahydrofuran; hexane / 0.42 h / Ambient temperature

5: 83 percent / amberlyst, methyl orthoformate / methanol / 48 h / Ambient temperature

6: 80 percent / MCPBA (75percent) / CH₂Cl₂ / 120 h / Ambient temperature

7: 3 mg / Lithium methoxide / benzene; xylene / 21 h / Heating

With n-butyllithium; Amberlyst; boron trifluoride diethyl etherate; lithium methanolate; hydrogen; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trimethyl orthoformate; Lindlar catalyst; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; xylene; benzene;

Reference yield:

3-methoxy-but-2-enoic acid ethyl ester (3510-99-4) → 4-Methoxy-5-[1-methoxy-1-((2S,3R)-3-phenyl-oxiranyl)-meth-(Z)-ylidene]-5H-furan-2-one (40072-82-0,67921-19-1,109009-80-5,109009-81-6,111767-57-8,111767-58-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 95 percent / NBS / 110 - 115 °C

2: 74 percent / anhydr. ZnBr₂ / xylene / 8 h / Heating

3: 5.7 g / n-butyl-lithium, diisopropylamide / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 0.33 h / -78 °C

4: 94 percent / tetrahydrofuran / -78 deg C, 1 h, 20 deg C, 1 h

5: 1.) BF₃*Et₂O / 1.)diethyl ether, -78 deg C, 2 h, 2.) -78 deg C, 1 h, RT_., 16 h

6: 85 percent / H₂ / Lindlar cat. / tetrahydrofuran; hexane / 0.42 h / Ambient temperature

7: 83 percent / amberlyst, methyl orthoformate / methanol / 48 h / Ambient temperature

8: 80 percent / MCPBA (75percent) / CH₂Cl₂ / 120 h / Ambient temperature

9: 3 mg / Lithium methoxide / benzene; xylene / 21 h / Heating

With N-Bromosuccinimide; n-butyllithium; Amberlyst; boron trifluoride diethyl etherate; lithium methanolate; hydrogen; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; zinc dibromide; trimethyl orthoformate; Lindlar catalyst; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; xylene; benzene;

Reference yield:

ethyl χ-bromo-β-methoxycrotonate (1116-51-4) → 4-Methoxy-5-[1-methoxy-1-((2S,3R)-3-phenyl-oxiranyl)-meth-(Z)-ylidene]-5H-furan-2-one (40072-82-0,67921-19-1,109009-80-5,109009-81-6,111767-57-8,111767-58-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 74 percent / anhydr. ZnBr₂ / xylene / 8 h / Heating

2: 5.7 g / n-butyl-lithium, diisopropylamide / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 0.33 h / -78 °C

3: 94 percent / tetrahydrofuran / -78 deg C, 1 h, 20 deg C, 1 h

4: 1.) BF₃*Et₂O / 1.)diethyl ether, -78 deg C, 2 h, 2.) -78 deg C, 1 h, RT_., 16 h

5: 85 percent / H₂ / Lindlar cat. / tetrahydrofuran; hexane / 0.42 h / Ambient temperature

6: 83 percent / amberlyst, methyl orthoformate / methanol / 48 h / Ambient temperature

7: 80 percent / MCPBA (75percent) / CH₂Cl₂ / 120 h / Ambient temperature

8: 3 mg / Lithium methoxide / benzene; xylene / 21 h / Heating

With n-butyllithium; Amberlyst; boron trifluoride diethyl etherate; lithium methanolate; hydrogen; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; zinc dibromide; trimethyl orthoformate; Lindlar catalyst; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; xylene; benzene;

upstream raw materials:

methyl 5-(cis-2',3'-epoxy-1',1'-dimethoxy-3'-phenylpropyl)tetronate

4-methoxy-5H-furan-2-one

3-methoxy-but-2-enoic acid ethyl ester

ethyl χ-bromo-β-methoxycrotonate

Downstream raw materials:

(+/-)-threo-7,8-dihydro-7,8-dihydroxypiperolid

Refernces