(1S^*,5S^*,6S^*,7R^*)-3-(2-benzyloxyethyl)-6-<3(R^*)-hydroxyoct-1(E)-enyl>-7-(tetrahydropyran-2-yl)oxybicyclo<3.3.0.>oct-2-ene

Base Information

• Chemical Name: (1S^*,5S^*,6S^*,7R^*)-3-(2-benzyloxyethyl)-6-<3(R^*)-hydroxyoct-1(E)-enyl>-7-(tetrahydropyran-2-yl)oxybicyclo<3.3.0.>oct-2-ene
• CAS No.: 112329-30-3
• Molecular Formula: C₃₀H₄₄O₄
• Molecular Weight: 468.677
• Mol file: 112329-30-3.mol

Synonyms:

Chemical Property of (1S^*,5S^*,6S^*,7R^*)-3-(2-benzyloxyethyl)-6-<3(R^*)-hydroxyoct-1(E)-enyl>-7-(tetrahydropyran-2-yl)oxybicyclo<3.3.0.>oct-2-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S^*,5S^*,6S^*,7R^*)-3-(2-benzyloxyethyl)-6-<3(R^*)-hydroxyoct-1(E)-enyl>-7-(tetrahydropyran-2-yl)oxybicyclo<3.3.0.>oct-2-ene

There total 38 articles about (1S^*,5S^*,6S^*,7R^*)-3-(2-benzyloxyethyl)-6-<3(R^*)-hydroxyoct-1(E)-enyl>-7-(tetrahydropyran-2-yl)oxybicyclo<3.3.0.>oct-2-ene 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: 33.0%

(1S*,5S*,6S*,7R*)-3-(2-benzyloxyethyl)-6-<3-oxo-1(E)-octenyl>-7-(tetrahydropyran-2-yl)oxybicyclo<3.3.0.>oct-2-ene (112329-29-0) → (1S*,5S*,6S*,7R*)-3-(2-benzyloxyethyl)-6-<3(S*)-hydroxyoct-1(E)-enyl>-7-(tetrahydropyran-2-yl)oxybicyclo<3.3.0.>oct-2-ene (112329-30-3,112419-88-2) + (1S*,5S*,6S*,7R*)-3-(2-benzyloxyethyl)-6-<3(R*)-hydroxyoct-1(E)-enyl>-7-(tetrahydropyran-2-yl)oxybicyclo<3.3.0.>oct-2-ene (112329-30-3,112419-88-2)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; for 0.5h;

DOI:10.1248/cpb.35.948

Reference yield: 33.0%

(1S*,5S*,6S*,7R*)-3-(2-benzyloxyethyl)-6-<3-oxo-1(E)-octenyl>-7-(tetrahydropyran-2-yl)oxybicyclo<3.3.0.>oct-2-ene (112329-29-0) → (1S*,5S*,6S*,7R*)-3-(2-benzyloxyethyl)-6-<3(S*)-hydroxyoct-1(E)-enyl>-7-(tetrahydropyran-2-yl)oxybicyclo<3.3.0.>oct-2-ene (112329-30-3,112419-88-2) + (1S*,5S*,6S*,7R*)-3-(2-benzyloxyethyl)-6-<3(R*)-hydroxyoct-1(E)-enyl>-7-(tetrahydropyran-2-yl)oxybicyclo<3.3.0.>oct-2-ene (112329-30-3,112419-88-2)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; for 0.5h;

DOI:10.1248/cpb.35.948

Reference yield:

(3aR,6aS)-7,7-(ethylidene acetal)bicyclo[3.3.0]octan-3-one (51716-62-2) → (1S*,5S*,6S*,7R*)-3-(2-benzyloxyethyl)-6-<3(S*)-hydroxyoct-1(E)-enyl>-7-(tetrahydropyran-2-yl)oxybicyclo<3.3.0.>oct-2-ene (112329-30-3,112419-88-2)

Guidance literature:

Multi-step reaction with 12 steps

1: 23.60 g / sodium hydride / 1,2-dimethoxy-ethane / 29 h / Ambient temperature

2: 15.05 g / lithium diisopropylamide / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.67 h / -78 °C

3: 12.42 g / lithium aluminum hydride / tetrahydrofuran / 0.42 h

4: 21.40 g / sodium hydride / dimethylformamide / 0.5 h / Ambient temperature

5: 2.100 g / conc.HCl / acetone / 1 h / Ambient temperature

6: 0.280 g / sodium hydride / dioxane / 0.5 h / 80 °C

7: 1.060 g / sodium borohydride / ethanol / 0.5 h

8: 79 percent / p-TsOH / CH₂Cl₂ / 0.5 h

9: 2.620 g / LiAlH₄ / tetrahydrofuran / 0.5 h

10: 2.061 g / SO₃ pyridine complex, Et₃N / dimethylsulfoxide / 0.75 h / Ambient temperature

11: 2.358 g / diethyl ether / 5 h / Ambient temperature

12: 65 percent / NaBH₄, CeCl₃*7H₂O / methanol / 0.5 h

With hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; cerium(III) chloride; sulfur trioxide pyridine complex; sodium hydride; toluene-4-sulfonic acid; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;

DOI:10.1248/cpb.35.948

upstream raw materials:

(1S^*,5S^*,6S^*,7R^*)-3-(2-benzyloxyethyl)-6-<3-oxo-1(E)-octenyl>-7-(tetrahydropyran-2-yl)oxybicyclo<3.3.0.>oct-2-ene

3,4-dihydro-2H-pyran

(3aR,6aS)-7,7-(ethylidene acetal)bicyclo[3.3.0]octan-3-one

benzyl bromide

Downstream raw materials:

(1S^*,5S^*,6S^*,7R^*)-3-(2-benzyloxyethyl)-6-<3(S^*)-(tetrahydropyran-2-yl)oxyoct-1(E)-enyl>-7-(tetrahydropyran-2-yl)oxybicyclo<3.3.0.>oct-2-ene

{2-[(3aS,5R,6R,6aS)-5-Hydroxy-6-((E)-(R)-3-hydroxy-oct-1-enyl)-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl]-ethoxy}-acetic acid

dl-3-oxa-9(O)-methano-Δ^6(9α)-prostaglandin I₁

Refernces