17-(4-azidophenyl)-15-dehydro-18,19,20-trinorisocarbacyclin methyl ester

Base Information

• Chemical Name: 17-(4-azidophenyl)-15-dehydro-18,19,20-trinorisocarbacyclin methyl ester
• CAS No.: 141887-92-5
• Molecular Formula: C₂₅H₃₁N₃O₄
• Molecular Weight: 437.539
• Mol file: 141887-92-5.mol

Synonyms:17-(4-azidophenyl)-15-dehydro-18,19,20-trinorisocarbacyclin methyl ester

Chemical Property of 17-(4-azidophenyl)-15-dehydro-18,19,20-trinorisocarbacyclin methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 17-(4-azidophenyl)-15-dehydro-18,19,20-trinorisocarbacyclin methyl ester

There total 7 articles about 17-(4-azidophenyl)-15-dehydro-18,19,20-trinorisocarbacyclin methyl 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:

isocarbacyclin (88931-51-5) → 17-(4-azidophenyl)-15-dehydro-18,19,20-trinorisocarbacyclin methyl ester (141887-92-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 93 percent / TBHP, L-(+)-DIPT, Ti(O-i-C₃H₇)4, molecular sieves / CH₂Cl₂; toluene / 6.5 h / -20 °C

2: 96 percent / pyridine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 48 h / 21 °C

3: 1) AcOH, H₂O, 2) 20percent aq. K₂CO₃ / 1) 100 deg C, 100 min, 2) r.t., 1 h

4: NaIO₄ / tetrahydrofuran; diethyl ether; H₂O / 1 h / Ambient temperature

5: 1) NaH / 1) DME, toluene, oil, r.t. 2) DME, toluene

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium periodate; molecular sieve; L-(+)-diisopropyl tartrate; water; sodium hydride; potassium carbonate; acetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; toluene;

DOI:10.1016/S0040-4020(01)88526-4

Reference yield:

13,14-epoxy-13,14-dihydroisocarbacyclin methyl ester (141978-72-5) → 17-(4-azidophenyl)-15-dehydro-18,19,20-trinorisocarbacyclin methyl ester (141887-92-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / pyridine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 48 h / 21 °C

2: 1) AcOH, H₂O, 2) 20percent aq. K₂CO₃ / 1) 100 deg C, 100 min, 2) r.t., 1 h

3: NaIO₄ / tetrahydrofuran; diethyl ether; H₂O / 1 h / Ambient temperature

4: 1) NaH / 1) DME, toluene, oil, r.t. 2) DME, toluene

With pyridine; dmap; sodium periodate; water; sodium hydride; potassium carbonate; acetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water;

DOI:10.1016/S0040-4020(01)88526-4

Reference yield:

13,14-dihydroxy-13,14-dihydroisocarbacyclin methyl ester (140900-70-5) → 17-(4-azidophenyl)-15-dehydro-18,19,20-trinorisocarbacyclin methyl ester (141887-92-5)

Guidance literature:

Multi-step reaction with 2 steps

1: NaIO₄ / tetrahydrofuran; diethyl ether; H₂O / 1 h / Ambient temperature

2: 1) NaH / 1) DME, toluene, oil, r.t. 2) DME, toluene

With sodium periodate; sodium hydride; In tetrahydrofuran; diethyl ether; water;

DOI:10.1016/S0040-4020(01)88526-4

upstream raw materials:

methyl (1R,5S,6S,7R)-6-formyl-7-hydroxybicyclo<3.3.0>oct-2-ene-3-pentanoate

4-(4-azidophenyl)-1-(dimethoxyphosphoryl)-2-butanone

isocarbacyclin

13,14-epoxy-13,14-dihydroisocarbacyclin methyl ester