(S)-2-((E)-(S)-1-Hydroxy-3-phenyl-allyl)-octanoic acid (1S,2R)-1-(toluene-4-sulfonylamino)-indan-2-yl ester

Base Information

• Chemical Name: (S)-2-((E)-(S)-1-Hydroxy-3-phenyl-allyl)-octanoic acid (1S,2R)-1-(toluene-4-sulfonylamino)-indan-2-yl ester
• CAS No.: 296242-28-9
• Molecular Formula: C₃₃H₃₉NO₅S
• Molecular Weight: 561.742
• Mol file: 296242-28-9.mol

Synonyms:(S)-2-((E)-(S)-1-Hydroxy-3-phenyl-allyl)-octanoic acid (1S,2R)-1-(toluene-4-sulfonylamino)-indan-2-yl ester

Chemical Property of (S)-2-((E)-(S)-1-Hydroxy-3-phenyl-allyl)-octanoic acid (1S,2R)-1-(toluene-4-sulfonylamino)-indan-2-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-((E)-(S)-1-Hydroxy-3-phenyl-allyl)-octanoic acid (1S,2R)-1-(toluene-4-sulfonylamino)-indan-2-yl ester

There total 4 articles about (S)-2-((E)-(S)-1-Hydroxy-3-phenyl-allyl)-octanoic acid (1S,2R)-1-(toluene-4-sulfonylamino)-indan-2-yl 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: 60.0%

(E)-3-phenylpropenal (14371-10-9) + Octanoic acid (1S,2R)-1-(toluene-4-sulfonylamino)-indan-2-yl ester (296242-29-0) → (S)-2-((E)-(S)-1-Hydroxy-3-phenyl-allyl)-octanoic acid (1S,2R)-1-(toluene-4-sulfonylamino)-indan-2-yl ester (296242-28-9)

Guidance literature:

Octanoic acid (1S,2R)-1-(toluene-4-sulfonylamino)-indan-2-yl ester; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 23 ℃;

(E)-3-phenylpropenal; With di-n-butylboryl trifluoromethanesulfonate; at -78 ℃; optical yield given as %de;

DOI:10.1055/s-0029-1216941

Reference yield:

(E)-3-phenylpropenal (14371-10-9) + Octanoic acid (1S,2R)-1-(toluene-4-sulfonylamino)-indan-2-yl ester (296242-29-0) → (S)-2-((E)-(S)-1-Hydroxy-3-phenyl-allyl)-octanoic acid (1S,2R)-1-(toluene-4-sulfonylamino)-indan-2-yl ester (296242-28-9) + 2-((E)-1-Hydroxy-3-phenyl-allyl)-octanoic acid (1S,2R)-1-(toluene-4-sulfonylamino)-indan-2-yl ester

Guidance literature:

Octanoic acid (1S,2R)-1-(toluene-4-sulfonylamino)-indan-2-yl ester; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 23 ℃; for 2h;

(E)-3-phenylpropenal; With di-n-butylboryl trifluoromethanesulfonate; In dichloromethane; at -78 ℃; Further stages.;

DOI:10.1021/ol000070a

Reference yield:

n-octanoic acid chloride (111-64-8) → (S)-2-((E)-(S)-1-Hydroxy-3-phenyl-allyl)-octanoic acid (1S,2R)-1-(toluene-4-sulfonylamino)-indan-2-yl ester (296242-28-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 92 percent / pyridine / CH₂Cl₂ / 2 h / 23 °C

2.1: TiCl₄; iPr₂NEt / CH₂Cl₂ / 2 h / 23 °C

2.2: Bu₂BOTf / CH₂Cl₂ / -78 °C

With pyridine; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; 1.1: Acylation / 2.1: Metallation / 2.2: Condensation;

DOI:10.1021/ol000070a

upstream raw materials:

(E)-3-phenylpropenal

Octanoic acid (1S,2R)-1-(toluene-4-sulfonylamino)-indan-2-yl ester

n-octanoic acid chloride

N-((1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl)-4-methylbenzenesulfonamide

Downstream raw materials:

(S)-2-((E)-(S)-1-Hydroxy-3-phenyl-allyl)-octanoic acid