(3aR,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-{(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-5-[4-(trityl-amino)-phenyl]-pent-1-enyl}-hexahydro-cyclopenta[b]furan-2-ol

Base Information

• Chemical Name: (3aR,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-{(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-5-[4-(trityl-amino)-phenyl]-pent-1-enyl}-hexahydro-cyclopenta[b]furan-2-ol
• CAS No.: 117625-43-1
• Molecular Formula: C₄₇H₅₅NO₆
• Molecular Weight: 729.957

Synonyms:

Chemical Property of (3aR,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-{(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-5-[4-(trityl-amino)-phenyl]-pent-1-enyl}-hexahydro-cyclopenta[b]furan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-{(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-5-[4-(trityl-amino)-phenyl]-pent-1-enyl}-hexahydro-cyclopenta[b]furan-2-ol

There total 10 articles about (3aR,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-{(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-5-[4-(trityl-amino)-phenyl]-pent-1-enyl}-hexahydro-cyclopenta[b]furan-2-ol 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:

(-)-Corey lactone 5-(4-phenylbenzoate) (31752-99-5) → (3aR,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-{(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-5-[4-(trityl-amino)-phenyl]-pent-1-enyl}-hexahydro-cyclopenta[b]furan-2-ol (117625-43-1)

Guidance literature:

Multi-step reaction with 6 steps

1: chromium trioxide-dipyridine complex, Celite / CH₂Cl₂ / 0.33 h / 0 °C

2: 1) NaH / 1) 1,2-dimethoxyethane, toluene, 25 deg C, 30 min, 2) 25 deg C, 2 h

3: 47 percent / NaBH₄, CeCl₃*7H₂O / methanol; tetrahydrofuran / 0.17 h / 25 °C

4: K₂CO₃, MeOH

5: PPTS

6: DiBAL

With methanol; sodium tetrahydroborate; cerium(III) chloride; 2,2'-bipyridine-chromium(VI) oxide; Celite; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm00121a046

Reference yield:

methyl 3-(4-aminophenyl)propionate (35418-07-6) → (3aR,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-{(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-5-[4-(trityl-amino)-phenyl]-pent-1-enyl}-hexahydro-cyclopenta[b]furan-2-ol (117625-43-1)

Guidance literature:

Multi-step reaction with 7 steps

1: pyridine / 20 h / 25 °C

2: 1) n-BuLi / 1) THF, hexane, -78 deg C, 30 min, 2) toluene, THF, -78 deg C, 30 min

3: 1) NaH / 1) 1,2-dimethoxyethane, toluene, 25 deg C, 30 min, 2) 25 deg C, 2 h

4: 47 percent / NaBH₄, CeCl₃*7H₂O / methanol; tetrahydrofuran / 0.17 h / 25 °C

5: K₂CO₃, MeOH

6: PPTS

7: DiBAL

With pyridine; methanol; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; In tetrahydrofuran; methanol;

DOI:10.1021/jm00121a046

Reference yield:

3-(4-aminophenyl)propionic acid (2393-17-1) → (3aR,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-{(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-5-[4-(trityl-amino)-phenyl]-pent-1-enyl}-hexahydro-cyclopenta[b]furan-2-ol (117625-43-1)

Guidance literature:

Multi-step reaction with 8 steps

1: HCl(g) / 20 h / Heating

2: pyridine / 20 h / 25 °C

3: 1) n-BuLi / 1) THF, hexane, -78 deg C, 30 min, 2) toluene, THF, -78 deg C, 30 min

4: 1) NaH / 1) 1,2-dimethoxyethane, toluene, 25 deg C, 30 min, 2) 25 deg C, 2 h

5: 47 percent / NaBH₄, CeCl₃*7H₂O / methanol; tetrahydrofuran / 0.17 h / 25 °C

6: K₂CO₃, MeOH

7: PPTS

8: DiBAL

With pyridine; hydrogenchloride; methanol; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; In tetrahydrofuran; methanol;

DOI:10.1021/jm00121a046

upstream raw materials:

(3aR,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-{(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-5-[4-(trityl-amino)-phenyl]-pent-1-enyl}-hexahydro-cyclopenta[b]furan-2-one

(-)-Corey lactone 5-(4-phenylbenzoate)

methyl 3-(4-aminophenyl)propionate

3-(4-aminophenyl)propionic acid

Downstream raw materials:

(Z)-7-((1R,2R,3R,5S)-5-Hydroxy-3-(tetrahydro-pyran-2-yloxy)-2-{(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-5-[4-(trityl-amino)-phenyl]-pent-1-enyl}-cyclopentyl)-hept-5-enoic acid

(Z)-7-{(1R,2R,3R,5S)-2-[(E)-(S)-5-(4-Azido-phenyl)-3-hydroxy-pent-1-enyl]-3,5-dihydroxy-cyclopentyl}-hept-5-enoic acid

(Z)-7-{(1R,2R,3R,5S)-2-[(E)-(S)-5-(4-Azido-phenyl)-3-hydroxy-pent-1-enyl]-3,5-dihydroxy-cyclopentyl}-hept-5-enoic acid methyl ester

(Z)-7-((1R,2R,3R,5S)-5-Hydroxy-3-(tetrahydro-pyran-2-yloxy)-2-{(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-5-[4-(trityl-amino)-phenyl]-pent-1-enyl}-cyclopentyl)-hept-5-enoic acid methyl ester

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