Toluene-4-sulfonic acid (Z)-(1S,2R)-1-((S)-1,2-dihydroxy-ethyl)-2-hydroxy-dec-4-enyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (Z)-(1S,2R)-1-((S)-1,2-dihydroxy-ethyl)-2-hydroxy-dec-4-enyl ester
• CAS No.: 76745-24-9
• Molecular Formula: C₁₉H₃₀O₆S
• Molecular Weight: 386.51
• Mol file: 76745-24-9.mol

Synonyms:Toluene-4-sulfonic acid (Z)-(1S,2R)-1-((S)-1,2-dihydroxy-ethyl)-2-hydroxy-dec-4-enyl ester

Chemical Property of Toluene-4-sulfonic acid (Z)-(1S,2R)-1-((S)-1,2-dihydroxy-ethyl)-2-hydroxy-dec-4-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (Z)-(1S,2R)-1-((S)-1,2-dihydroxy-ethyl)-2-hydroxy-dec-4-enyl ester

There total 4 articles about Toluene-4-sulfonic acid (Z)-(1S,2R)-1-((S)-1,2-dihydroxy-ethyl)-2-hydroxy-dec-4-enyl 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:

Toluene-4-sulfonic acid (Z)-(1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-dec-4-enyl ester (76745-23-8) → Toluene-4-sulfonic acid (Z)-(1S,2R)-1-((S)-1,2-dihydroxy-ethyl)-2-hydroxy-dec-4-enyl ester (76745-24-9)

Guidance literature:

With hydrogenchloride; at 23 ℃; for 8h;

DOI:10.1021/ja00547a051

Reference yield:

hexylidenetriphenylphosphoran (16666-79-8,19493-12-0) → Toluene-4-sulfonic acid (Z)-(1S,2R)-1-((S)-1,2-dihydroxy-ethyl)-2-hydroxy-dec-4-enyl ester (76745-24-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / hexamethylphosphoric triamide / tetrahydrofuran / 1.) -78 deg C, 0.5 h, 2.) -78 deg C to -20 deg C, 3 h, 3.) -20 deg C, 72 h

2: 97 percent / pyridine / 96 h / 23 °C

3: 10percent methanolic HCl / 8 h / 23 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; pyridine;

DOI:10.1021/ja00547a051

Reference yield:

(4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetrahydro-furan-2-ol → Toluene-4-sulfonic acid (Z)-(1S,2R)-1-((S)-1,2-dihydroxy-ethyl)-2-hydroxy-dec-4-enyl ester (76745-24-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / hexamethylphosphoric triamide / tetrahydrofuran / 1.) -78 deg C, 0.5 h, 2.) -78 deg C to -20 deg C, 3 h, 3.) -20 deg C, 72 h

2: 97 percent / pyridine / 96 h / 23 °C

3: 10percent methanolic HCl / 8 h / 23 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; pyridine;

DOI:10.1021/ja00547a051

upstream raw materials:

Toluene-4-sulfonic acid (Z)-(1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-dec-4-enyl ester

hexylidenetriphenylphosphoran

(Z)-(1R,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-dec-4-en-1-ol

Downstream raw materials:

methyl 5(S)-(benzoyloxy)-12(R)-hydroxy-6(Z),8(E),10(E),14(Z)-eicosatetraenoate

(R)-1-[(2S,3R)-((Z)-3-Oct-2-enyl)-oxiranyl]-ethane-1,2-diol

((2E,4E,8Z)-(R)-6-Hydroxy-tetradeca-2,4,8-trienyl)-triphenyl-phosphonium; bromide

6-trans-Leukotriene B₄