EP-171

Base Information

• Chemical Name: EP-171
• CAS No.: 122089-44-5
• Molecular Formula: C₂₃H₂₉FO₅
• Molecular Weight: 404.479
• Mol file: 122089-44-5.mol

Synonyms:5-Heptenoicacid, 7-[(1R,2S,3S,4S)-3-[(1E,3S)-4-(4-fluorophenoxy)-3-hydroxy-1-butenyl]-7-oxabicyclo[2.2.1]hept-2-yl]-,(5Z)-rel- (9CI); 5-Heptenoic acid,7-[3-[4-(4-fluorophenoxy)-3-hydroxy-1-butenyl]-7-oxabicyclo[2.2.1]hept-2-yl]-,[1a,2a(Z),3b(1E,3S*),4a]-(?à)-; 5-Heptenoic acid, 7-[3-[4-(4-fluorophenoxy)-3-hydroxy-1-butenyl]-7-oxabicyclo[2.2.1]hept-2-yl]-,[1a,2a(Z),3b(1E,3S*),4a]-;EP 171; EP 171 (activator)

Chemical Property of EP-171

Chemical Property:

• Boiling Point: 585.4±50.0 °C(Predicted)
• PKA: 4.76±0.10(Predicted)
• Density: 1.235±0.06 g/cm3(Predicted)

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of EP-171

There total 40 articles about EP-171 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:

2α-hydroxymethyl-3α-vinyl-7α-oxabicyclo<2.2.1>heptane (119119-31-2,141900-13-2) → 3α-(6-carboxyhex-2Z-enyl)-2α-(3-hydroxy-4-p-fluorophenoxy-but-1E-enyl)-7α-oxabicyclo<2.2.1>heptane (115825-93-9,119238-77-6,119238-78-7,119238-79-8,122089-44-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) DCC, DMSO 2.) pyridinium trifluoroacetate / 1.) benzene, room t., 2.) benzene, 70 deg C, 20 min

2: DBU / CHCl₃ / 1 h / Ambient temperature

3: CH(OMe)3 / p-Tos-OH / 48 h / Ambient temperature

4: 1.) 0.5 M 9-BBN(THF) 2.) 3 M aq. NaOH, 30percent H₂O₂ / 1.) THF, 0 deg C to room t., 90 min, 2.) THF, 0 deg C, 15 min

5: 76 percent / PCC, NaOAc / CH₂Cl₂ / 2 h / 23 °C

6: 1.) BuLi(hexane) / 1.) DMSO, with cooling, then 10 min, 23 deg C, 2.) DMSO, 23 deg C

7: 50percent aq. HCl / CHCl₃; propan-2-ol / 0.5 h

8: 1.) NaH / 1.) THF, 23 deg C, 1 h 2.) THF, 0 deg C, then 45 deg C, 3 h

9: 7.6 mg / NaBH₄ / ethanol / -20 °C

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; 9-BBN-THF; dihydrogen peroxide; sodium acetate; pyridinium trifluroacetate; sodium hydride; dimethyl sulfoxide; dicyclohexyl-carbodiimide; pyridinium chlorochromate; trimethyl orthoformate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In ethanol; dichloromethane; chloroform; isopropyl alcohol;

DOI:10.1016/0223-5234(88)90209-7

Reference yield:

2α-hydroxymethyl-3α-vinyl-7α-oxabicyclo<2.2.1>heptane (119119-31-2,141900-13-2) → 3α-(6-carboxyhex-2Z-enyl)-2β-(3-hydroxy-4-p-fluorophenoxy-but-1E-enyl)-7α-oxabicyclo<2.2.1>heptane (115825-93-9,119238-77-6,119238-78-7,119238-79-8,122089-44-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) DCC, DMSO 2.) pyridinium trifluoroacetate / 1.) benzene, room t., 2.) benzene, 70 deg C, 20 min

2: DBU / CHCl₃ / 1 h / Ambient temperature

3: CH(OMe)3 / p-Tos-OH / 48 h / Ambient temperature

4: 1.) 0.5 M 9-BBN(THF) 2.) 3 M aq. NaOH, 30percent H₂O₂ / 1.) THF, 0 deg C to room t., 90 min, 2.) THF, 0 deg C, 15 min

5: 76 percent / PCC, NaOAc / CH₂Cl₂ / 2 h / 23 °C

6: 1.) BuLi(hexane) / 1.) DMSO, with cooling, then 10 min, 23 deg C, 2.) DMSO, 23 deg C

7: 50percent aq. HCl / CHCl₃; propan-2-ol / 0.5 h

8: 1.) NaH / 1.) THF, 23 deg C, 1 h 2.) THF, 0 deg C, then 45 deg C, 3 h

9: 25 mg / NaBH₄ / ethanol / -20 °C

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; 9-BBN-THF; dihydrogen peroxide; sodium acetate; pyridinium trifluroacetate; sodium hydride; dimethyl sulfoxide; dicyclohexyl-carbodiimide; pyridinium chlorochromate; trimethyl orthoformate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In ethanol; dichloromethane; chloroform; isopropyl alcohol;

DOI:10.1016/0223-5234(88)90209-7

Reference yield:

2α-hydroxymethyl-3α-vinyl-7α-oxabicyclo<2.2.1>heptane (119119-31-2,141900-13-2) → 3α-(6-carboxyhex-2Z-enyl)-2β-(3-hydroxy-4-p-fluorophenoxy-but-1E-enyl)-7α-oxabicyclo<2.2.1>heptane (115825-93-9,119238-77-6,119238-78-7,119238-79-8,122089-44-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) DCC, DMSO 2.) pyridinium trifluoroacetate / 1.) benzene, room t., 2.) benzene, 70 deg C, 20 min

2: DBU / CHCl₃ / 1 h / Ambient temperature

3: CH(OMe)3 / p-Tos-OH / 48 h / Ambient temperature

4: 1.) 0.5 M 9-BBN(THF) 2.) 3 M aq. NaOH, 30percent H₂O₂ / 1.) THF, 0 deg C to room t., 90 min, 2.) THF, 0 deg C, 15 min

5: 76 percent / PCC, NaOAc / CH₂Cl₂ / 2 h / 23 °C

6: 1.) BuLi(hexane) / 1.) DMSO, with cooling, then 10 min, 23 deg C, 2.) DMSO, 23 deg C

7: 50percent aq. HCl / CHCl₃; propan-2-ol / 0.5 h

8: 1.) NaH / 1.) THF, 23 deg C, 1 h 2.) THF, 0 deg C, then 45 deg C, 3 h

9: 27 mg / NaBH₄ / ethanol / -20 °C

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; 9-BBN-THF; dihydrogen peroxide; sodium acetate; pyridinium trifluroacetate; sodium hydride; dimethyl sulfoxide; dicyclohexyl-carbodiimide; pyridinium chlorochromate; trimethyl orthoformate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In ethanol; dichloromethane; chloroform; isopropyl alcohol;

DOI:10.1016/0223-5234(88)90209-7

upstream raw materials:

3α-(6-carboxy-hex-2Z-enyl)-2β-(4-p-fluorophenoxybut-1E-en-3-onyl)-7α-oxabicyclo<2.2.1>heptane

(4-carboxybutyl)triphenylphosphonium bromide

2α-hydroxymethyl-3α-vinyl-7α-oxabicyclo<2.2.1>heptane

2β-dimethoxymethyl-3α-(2-hydroxyethyl)-7α-oxabicyclo<2.2.1>heptane

Refernces