(3aR,4R,5R,6aS)-4-[(E)-(R)-4-[2-(tert-Butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenoxy]-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-one

Base Information

• Chemical Name: (3aR,4R,5R,6aS)-4-[(E)-(R)-4-[2-(tert-Butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenoxy]-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-one
• CAS No.: 117625-75-9
• Molecular Formula: C₅₂H₆₅NO₈Si
• Molecular Weight: 860.176

Synonyms:

Chemical Property of (3aR,4R,5R,6aS)-4-[(E)-(R)-4-[2-(tert-Butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenoxy]-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4R,5R,6aS)-4-[(E)-(R)-4-[2-(tert-Butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenoxy]-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-one

There total 13 articles about (3aR,4R,5R,6aS)-4-[(E)-(R)-4-[2-(tert-Butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenoxy]-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-one 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)-4-[(E)-(R)-4-[2-(tert-Butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenoxy]-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-one (117625-75-9)

Guidance literature:

Multi-step reaction with 5 steps

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

2: 1) NaH

3: NaBH₄, CeCl₃

4: K₂CO₃, MeOH

5: PPTS

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

DOI:10.1021/jm00121a046

Reference yield:

1,2-dihydroxy-4-nitrobenzene (3316-09-4) → (3aR,4R,5R,6aS)-4-[(E)-(R)-4-[2-(tert-Butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenoxy]-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-one (117625-75-9)

Guidance literature:

Multi-step reaction with 9 steps

1: Et₃N

2: imidazole

3: H₂ / Pd-C

4: Py

5: 1) n-BuLi

6: 1) NaH

7: NaBH₄, CeCl₃

8: K₂CO₃, MeOH

9: PPTS

With pyridine; 1H-imidazole; methanol; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; triethylamine; palladium on activated charcoal;

DOI:10.1021/jm00121a046

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (3aR,4R,5R,6aS)-4-[(E)-(R)-4-[2-(tert-Butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenoxy]-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-one (117625-75-9)

Guidance literature:

Multi-step reaction with 8 steps

1: imidazole

2: H₂ / Pd-C

3: Py

4: 1) n-BuLi

5: 1) NaH

6: NaBH₄, CeCl₃

7: K₂CO₃, MeOH

8: PPTS

With pyridine; 1H-imidazole; methanol; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; palladium on activated charcoal;

DOI:10.1021/jm00121a046

upstream raw materials:

3,4-dihydro-2H-pyran

(3aR,4R,5R,6aS)-4-{(E)-(R)-4-[2-(tert-Butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenoxy]-3-hydroxy-but-1-enyl}-5-hydroxy-hexahydro-cyclopenta[b]furan-2-one

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

1,2-dihydroxy-4-nitrobenzene

Downstream raw materials:

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

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

(Z)-7-[(1R,2R,3R,5S)-2-[(E)-(R)-4-[2-(tert-Butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenoxy]-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-hydroxy-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid

(Z)-7-[(1R,2R,3R,5S)-2-[(E)-(R)-4-[2-(tert-Butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenoxy]-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-hydroxy-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester

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