(4S,5S)-3-[1-Hydroxy-meth-(Z)-ylidene]-4-[2-(3-methoxy-bicyclo[4.2.0]octa-1,3,5-trien-7-yl)-1-(toluene-4-sulfonyl)-ethyl]-5-methoxymethyl-dihydro-furan-2-one

Base Information

• Chemical Name: (4S,5S)-3-[1-Hydroxy-meth-(Z)-ylidene]-4-[2-(3-methoxy-bicyclo[4.2.0]octa-1,3,5-trien-7-yl)-1-(toluene-4-sulfonyl)-ethyl]-5-methoxymethyl-dihydro-furan-2-one
• CAS No.: 99598-50-2
• Molecular Formula: C₂₅H₂₈O₇S
• Molecular Weight: 472.559
• Mol file: 99598-50-2.mol

Synonyms:

Chemical Property of (4S,5S)-3-[1-Hydroxy-meth-(Z)-ylidene]-4-[2-(3-methoxy-bicyclo[4.2.0]octa-1,3,5-trien-7-yl)-1-(toluene-4-sulfonyl)-ethyl]-5-methoxymethyl-dihydro-furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-3-[1-Hydroxy-meth-(Z)-ylidene]-4-[2-(3-methoxy-bicyclo[4.2.0]octa-1,3,5-trien-7-yl)-1-(toluene-4-sulfonyl)-ethyl]-5-methoxymethyl-dihydro-furan-2-one

There total 3 articles about (4S,5S)-3-[1-Hydroxy-meth-(Z)-ylidene]-4-[2-(3-methoxy-bicyclo[4.2.0]octa-1,3,5-trien-7-yl)-1-(toluene-4-sulfonyl)-ethyl]-5-methoxymethyl-dihydro-furan-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:

2-(4-methoxybenzocyclobutenyl)ethyl p-toluenesulfonate (60100-24-5) → (4S,5S)-3-[1-Hydroxy-meth-(Z)-ylidene]-4-[2-(3-methoxy-bicyclo[4.2.0]octa-1,3,5-trien-7-yl)-1-(toluene-4-sulfonyl)-ethyl]-5-methoxymethyl-dihydro-furan-2-one (99598-50-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / sodium p-toluenesulfinate, sodium iodide / dimethylformamide / 2 h / 80 °C

2: 1.) lithium diisopropylamide; 2.) hexamethylphosphoramide / 1.) tetrahydrofuran, -78 deg C, 1 h; 2.) tetrahydrofuran, -78 deg C, 2 h

3: 1.) 60percent sodium hydride; 2.) 10percent hydrochloric acid / 1.) benzene, r.t., 30 min; 2.) 8 h, r.t., water

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydride; sodium 4-methylbenzenesulfinate; sodium iodide; lithium diisopropyl amide; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)96631-1

Reference yield:

2-(4-methoxybenzocyclobutenyl)ethyl p-tolyl sulfone (99598-48-8) → (4S,5S)-3-[1-Hydroxy-meth-(Z)-ylidene]-4-[2-(3-methoxy-bicyclo[4.2.0]octa-1,3,5-trien-7-yl)-1-(toluene-4-sulfonyl)-ethyl]-5-methoxymethyl-dihydro-furan-2-one (99598-50-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) lithium diisopropylamide; 2.) hexamethylphosphoramide / 1.) tetrahydrofuran, -78 deg C, 1 h; 2.) tetrahydrofuran, -78 deg C, 2 h

2: 1.) 60percent sodium hydride; 2.) 10percent hydrochloric acid / 1.) benzene, r.t., 30 min; 2.) 8 h, r.t., water

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydride; lithium diisopropyl amide;

DOI:10.1016/S0040-4020(01)96631-1

Reference yield:

4β-<2-(4-methoxybenzocyclobutenyl)-1-p-toluenesulfinyl>-ethyl-5α-methoxymethyl-furan-2-one (99598-49-9) + formic acid ethyl ester (109-94-4) → (4S,5S)-3-[1-Hydroxy-meth-(Z)-ylidene]-4-[2-(3-methoxy-bicyclo[4.2.0]octa-1,3,5-trien-7-yl)-1-(toluene-4-sulfonyl)-ethyl]-5-methoxymethyl-dihydro-furan-2-one (99598-50-2)

Guidance literature:

With hydrogenchloride; sodium hydride; Yield given. Multistep reaction; 1.) benzene, r.t., 30 min; 2.) 8 h, r.t., water;

DOI:10.1016/S0040-4020(01)96631-1

upstream raw materials:

4β-<2-(4-methoxybenzocyclobutenyl)-1-p-toluenesulfinyl>-ethyl-5α-methoxymethyl-furan-2-one

formic acid ethyl ester

2-(4-methoxybenzocyclobutenyl)ethyl p-toluenesulfonate

2-(4-methoxybenzocyclobutenyl)ethyl p-tolyl sulfone

Downstream raw materials:

trans-4,5-(4-methoxybenzo)-1β,7aβ-(2α-methoxymethyl-5-oxofuro)-7-phenylthio-2-p-toluenesulfinylhydrindane

cis-4,5-(4-methoxybenzo)-1β,7aβ-(2α-methoxymethyl-5-oxofuro)-7-phenylthio-2-p-toluenesulfinylhydrindane

trans-4,5-(4-methoxybenzo)-1β,7aβ-(5α-methoxy-2α-methoxymethylfuro)-7-phenylthio-2-p-toluenesulfinylhydrindane

cis-4,5-(4-methoxybenzo)-1β,7aβ-(5α-methoxy-2α-methoxymethylfuro)-7-phenylthio-2-p-toluenesulfinylhydrindane