Acetic acid (E)-(1S,2R,3S)-3-acetoxy-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-5-phenyl-pent-4-enyl ester

Base Information

• Chemical Name: Acetic acid (E)-(1S,2R,3S)-3-acetoxy-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-5-phenyl-pent-4-enyl ester
• CAS No.: 307492-66-6
• Molecular Formula: C₂₇H₃₄O₆
• Molecular Weight: 454.563
• Mol file: 307492-66-6.mol

Synonyms:Acetic acid (E)-(1S,2R,3S)-3-acetoxy-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-5-phenyl-pent-4-enyl ester

Chemical Property of Acetic acid (E)-(1S,2R,3S)-3-acetoxy-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-5-phenyl-pent-4-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (E)-(1S,2R,3S)-3-acetoxy-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-5-phenyl-pent-4-enyl ester

There total 7 articles about Acetic acid (E)-(1S,2R,3S)-3-acetoxy-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-5-phenyl-pent-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: 84.0%

acetic anhydride (108-24-7) + (E)-(3S,4R,5S,6S)-7-(4-Methoxy-benzyloxy)-4,6-dimethyl-1-phenyl-hept-1-ene-3,5-diol (307492-63-3) → Acetic acid (E)-(1S,2R,3S)-3-acetoxy-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-5-phenyl-pent-4-enyl ester (307492-66-6)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1016/S0040-4039(00)02002-5

Reference yield:

(E)-3-phenylpropenal (14371-10-9) → Acetic acid (E)-(1S,2R,3S)-3-acetoxy-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-5-phenyl-pent-4-enyl ester (307492-66-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Sn(OTf)2; triethylamine / CH₂Cl₂ / 2 h / -78 °C

1.2: 86 percent / CH₂Cl₂ / 1 h / -78 °C

2.1: 96 percent / Me₄NHB(OAc)3; AcOH / acetonitrile / 21 h / -40 - -20 °C

3.1: 84 percent / pyridine; DMAP / CH₂Cl₂ / 1.5 h / 20 °C

With pyridine; dmap; tin(II) trifluoromethanesulfonate; acetic acid; triethylamine; tetramethylammonium triacetoxyborohydride; In dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(00)02002-5

Reference yield:

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → Acetic acid (E)-(1S,2R,3S)-3-acetoxy-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-5-phenyl-pent-4-enyl ester (307492-66-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 81 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 17 h / 20 °C

2.1: 90 percent / tetrahydrofuran; diethyl ether / 1 h

3.1: Sn(OTf)2; triethylamine / CH₂Cl₂ / 2 h / -78 °C

3.2: 86 percent / CH₂Cl₂ / 1 h / -78 °C

4.1: 96 percent / Me₄NHB(OAc)3; AcOH / acetonitrile / 21 h / -40 - -20 °C

5.1: 84 percent / pyridine; DMAP / CH₂Cl₂ / 1.5 h / 20 °C

With pyridine; dmap; tin(II) trifluoromethanesulfonate; (1S)-10-camphorsulfonic acid; acetic acid; triethylamine; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(00)02002-5

upstream raw materials:

acetic anhydride

(E)-(3S,4R,5S,6S)-7-(4-Methoxy-benzyloxy)-4,6-dimethyl-1-phenyl-hept-1-ene-3,5-diol

(E)-3-phenylpropenal

O-(4-methoxybenzyl)-trichloroacetimidate

Downstream raw materials:

(1R,4R,5R,6S,E)-7-(tert-butyldiphenylsilyloxy)-4,6-dimethyl-1-phenylhept-1-ene-3,5-diyl diacetate

(3S,4R,5S,6S,E)-7-(tert-butyldiphenylsilyloxy)-4,6-dimethyl-1-phenylhept-1-ene-3,5-diol

Acetic acid (E)-(1S,2R,3S)-3-acetoxy-1-((S)-2-hydroxy-1-methyl-ethyl)-2-methyl-5-phenyl-pent-4-enyl ester