Biphenyl-4-carboxylic acid 2-{(1R,2S,3R,5R)-3,5-bis-benzyloxy-2-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-ethyl ester

Base Information

• Chemical Name: Biphenyl-4-carboxylic acid 2-{(1R,2S,3R,5R)-3,5-bis-benzyloxy-2-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-ethyl ester
• CAS No.: 88365-24-6
• Molecular Formula: C₄₇H₅₆O₆
• Molecular Weight: 716.958
• Mol file: 88365-24-6.mol

Synonyms:

Chemical Property of Biphenyl-4-carboxylic acid 2-{(1R,2S,3R,5R)-3,5-bis-benzyloxy-2-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Biphenyl-4-carboxylic acid 2-{(1R,2S,3R,5R)-3,5-bis-benzyloxy-2-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-ethyl ester

There total 14 articles about Biphenyl-4-carboxylic acid 2-{(1R,2S,3R,5R)-3,5-bis-benzyloxy-2-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-ethyl 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:

dimethyl 2-oxoheptylphosphonate (36969-89-8) → Biphenyl-4-carboxylic acid 2-{(1R,2S,3R,5R)-3,5-bis-benzyloxy-2-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-ethyl ester (88365-24-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) NaH (80percent in oil) / 1) anh. DME, r. t., 1 h, 2) DME, 40 deg C, 4 h

2: 93 percent / pyridine / 1) 1 h, 0 deg C, 2) 1 h, r. t.

3: 38 percent / ZnCl₂; NaBH₄ / 1,2-dimethoxy-ethane / 1) 1.5 h, -20 deg C, 2) 1 h, 0 deg C, 3) 3 h, r. t.

4: 2percent p-toluenesulfonic acid / CH₂Cl₂; tetrahydrofuran / 3 h

With sodium tetrahydroborate; sodium hydride; toluene-4-sulfonic acid; zinc(II) chloride; In tetrahydrofuran; pyridine; 1,2-dimethoxyethane; dichloromethane;

DOI:10.1002/jlac.198319831215

Reference yield:

benzyl bromide (100-39-0) → Biphenyl-4-carboxylic acid 2-{(1R,2S,3R,5R)-3,5-bis-benzyloxy-2-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-ethyl ester (88365-24-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 1) NaH (80percent in oil) / 1) DMF, 0.5 h, -5 deg C, 2) 3 h, r. t.

2: 90 percent / Hg(II)-acetate, Hg(II)-oxide / H₂O; acetone / 1 h

3: 1) NaH (80percent in oil) / 1) anh. DME, r. t., 1 h, 2) DME, 40 deg C, 4 h

4: 93 percent / pyridine / 1) 1 h, 0 deg C, 2) 1 h, r. t.

5: 38 percent / ZnCl₂; NaBH₄ / 1,2-dimethoxy-ethane / 1) 1.5 h, -20 deg C, 2) 1 h, 0 deg C, 3) 3 h, r. t.

6: 2percent p-toluenesulfonic acid / CH₂Cl₂; tetrahydrofuran / 3 h

With sodium tetrahydroborate; mercury(II) diacetate; sodium hydride; toluene-4-sulfonic acid; mercury(II) oxide; zinc(II) chloride; In tetrahydrofuran; pyridine; 1,2-dimethoxyethane; dichloromethane; water; acetone;

DOI:10.1002/jlac.198319831215

Reference yield:

(6R,7R)-(-)-7-Hydroxy-3-oxabicyclo<4.3.0>non-1-en-9-on (74552-31-1) → Biphenyl-4-carboxylic acid 2-{(1R,2S,3R,5R)-3,5-bis-benzyloxy-2-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-ethyl ester (88365-24-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 16 g / TEA / tetrahydrofuran / 5 h / Ambient temperature

2: 11.3 g / LiAlH₄ / tetrahydrofuran / 1.5 h / 0 °C

3: 1) NaH (80percent in oil) / 1) DMF, 0.5 h, -5 deg C, 2) 3 h, r. t.

4: 90 percent / Hg(II)-acetate, Hg(II)-oxide / H₂O; acetone / 1 h

5: 1) NaH (80percent in oil) / 1) anh. DME, r. t., 1 h, 2) DME, 40 deg C, 4 h

6: 93 percent / pyridine / 1) 1 h, 0 deg C, 2) 1 h, r. t.

7: 38 percent / ZnCl₂; NaBH₄ / 1,2-dimethoxy-ethane / 1) 1.5 h, -20 deg C, 2) 1 h, 0 deg C, 3) 3 h, r. t.

8: 2percent p-toluenesulfonic acid / CH₂Cl₂; tetrahydrofuran / 3 h

With sodium tetrahydroborate; lithium aluminium tetrahydride; TEA; mercury(II) diacetate; sodium hydride; toluene-4-sulfonic acid; mercury(II) oxide; zinc(II) chloride; In tetrahydrofuran; pyridine; 1,2-dimethoxyethane; dichloromethane; water; acetone;

DOI:10.1002/jlac.198319831215

upstream raw materials:

3,4-dihydro-2H-pyran

Biphenyl-4-carboxylic acid 2-[(1R,2R,3R,5R)-3,5-bis-benzyloxy-2-((E)-3-hydroxy-oct-1-enyl)-cyclopentyl]-ethyl ester

9,11-Dibenzyl-2-decarboxy-6-(p-phenylbenzoyloxy)-2,3,4,5-tetranor-12-epi-PGF_1β

dimethyl 2-oxoheptylphosphonate

Downstream raw materials:

2-{(1R,2R,3R,5R)-3,5-Bis-benzyloxy-2-[(E)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-ethanol

2-{(1R,2S,3R,5R)-3,5-Bis-benzyloxy-2-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-ethanol

(Z)-7-{(1R,2S,3R,5R)-3,5-Bis-benzyloxy-2-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-hept-5-enoic acid

(Z)-7-[(1R,2S,3R,5R)-3,5-Bis-benzyloxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-cyclopentyl]-hept-5-enoic acid