(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

Base Information

• Chemical Name: (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
• CAS No.: 117625-77-1
• Molecular Formula: C₅₇H₇₅NO₉Si
• Molecular Weight: 946.309

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 15 articles about (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 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) → (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 (117625-77-1)

Guidance literature:

Multi-step reaction with 7 steps

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

2: 1) NaH

3: NaBH₄, CeCl₃

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 dichloromethane;

DOI:10.1021/jm00121a046

Reference yield:

1,2-dihydroxy-4-nitrobenzene (3316-09-4) → (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 (117625-77-1)

Guidance literature:

Multi-step reaction with 11 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

10: DIBAL

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

DOI:10.1021/jm00121a046

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (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 (117625-77-1)

Guidance literature:

Multi-step reaction with 10 steps

1: imidazole

2: H₂ / Pd-C

3: Py

4: 1) n-BuLi

5: 1) NaH

6: NaBH₄, CeCl₃

7: K₂CO₃, MeOH

8: PPTS

9: DIBAL

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

DOI:10.1021/jm00121a046

upstream raw materials:

(4-carboxybutyl)triphenylphosphonium bromide

(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-ol

(-)-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 methyl ester

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