(R)-(-)-{2-[5-but-3-enyl-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]-2-oxoethyl}phosphonic acid dimethyl ester

Base Information

• Chemical Name: (R)-(-)-{2-[5-but-3-enyl-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]-2-oxoethyl}phosphonic acid dimethyl ester
• CAS No.: 853356-48-6
• Molecular Formula: C₁₉H₂₆NO₆PS
• Molecular Weight: 427.458
• Mol file: 853356-48-6.mol

Synonyms:(R)-(-)-{2-[5-but-3-enyl-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]-2-oxoethyl}phosphonic acid dimethyl ester

Chemical Property of (R)-(-)-{2-[5-but-3-enyl-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]-2-oxoethyl}phosphonic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-(-)-{2-[5-but-3-enyl-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]-2-oxoethyl}phosphonic acid dimethyl ester

There total 7 articles about (R)-(-)-{2-[5-but-3-enyl-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]-2-oxoethyl}phosphonic acid dimethyl ester 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: 41.0%

(R)-(-)-5-but-3-enyl-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrole-2-carboxylic acid methyl ester (853356-45-3) + dimethyl methane phosphonate (756-79-6) → (R)-(-)-{2-[5-but-3-enyl-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]-2-oxoethyl}phosphonic acid dimethyl ester (853356-48-6)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at 25 ℃; for 4h;

DOI:10.1021/jo0504058

Reference yield:

(S)-Pyroglutaminol (17342-08-4) → (R)-(-)-{2-[5-but-3-enyl-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]-2-oxoethyl}phosphonic acid dimethyl ester (853356-48-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 64 percent / 4-(dimethylamino)pyridine; Et₃N / CH₂Cl₂ / 16 h / 20 °C

2.1: 61 percent / diethyl ether; tetrahydrofuran / 3 h / Heating

3.1: 59 percent / n-BuLi / tetrahydrofuran; hexane / 3 h / -78 - 20 °C

4.1: KHMDS / toluene; tetrahydrofuran / 1.5 h / -78 °C

4.2: toluene; tetrahydrofuran / 1 h / -78 °C

5.1: 65 percent / PPh₃; Et₃N / Pd(OAc)2 / dimethylformamide / 4 h / 40 °C

6.1: 41 percent / n-BuLi / hexane; tetrahydrofuran / 4 h / 25 °C

With dmap; n-butyllithium; potassium hexamethylsilazane; triethylamine; triphenylphosphine; palladium diacetate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 6.1: Horner-Emmons-Wadsworth reaction;

DOI:10.1021/jo0504058

Reference yield:

(R)-5-(but-3-en-1-yl)pyrrolidin-2-one (633294-91-4) → (R)-(-)-{2-[5-but-3-enyl-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]-2-oxoethyl}phosphonic acid dimethyl ester (853356-48-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 59 percent / n-BuLi / tetrahydrofuran; hexane / 3 h / -78 - 20 °C

2.1: KHMDS / toluene; tetrahydrofuran / 1.5 h / -78 °C

2.2: toluene; tetrahydrofuran / 1 h / -78 °C

3.1: 65 percent / PPh₃; Et₃N / Pd(OAc)2 / dimethylformamide / 4 h / 40 °C

4.1: 41 percent / n-BuLi / hexane; tetrahydrofuran / 4 h / 25 °C

With n-butyllithium; potassium hexamethylsilazane; triethylamine; triphenylphosphine; palladium diacetate; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; toluene; 4.1: Horner-Emmons-Wadsworth reaction;

DOI:10.1021/jo0504058

upstream raw materials:

(R)-(-)-5-but-3-enyl-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrole-2-carboxylic acid methyl ester

dimethyl methane phosphonate

(R)-5-(but-3-en-1-yl)pyrrolidin-2-one

(R)-(-)-5-but-3-enyl-1-(toluene-4-sulfonyl)pyrrolidin-2-one

Downstream raw materials:

(R)-(-)-[5-but-3-enyl-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]-4-methylpent-2-en-1-one

(2R,4S)-(+)-2-but-3-enyl-4-isopropyl-1-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-cyclopenta[b]pyrrol-6-one