Benzoic acid (3aR,4R,5R,6aS)-4-{(E)-(R)-5-[2-(tert-butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenyl]-3-hydroxy-pent-1-enyl}-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

Base Information

• Chemical Name: Benzoic acid (3aR,4R,5R,6aS)-4-{(E)-(R)-5-[2-(tert-butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenyl]-3-hydroxy-pent-1-enyl}-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester
• CAS No.: 117706-92-0
• Molecular Formula: C₅₀H₅₅NO₆Si
• Molecular Weight: 794.075

Synonyms:

Chemical Property of Benzoic acid (3aR,4R,5R,6aS)-4-{(E)-(R)-5-[2-(tert-butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenyl]-3-hydroxy-pent-1-enyl}-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (3aR,4R,5R,6aS)-4-{(E)-(R)-5-[2-(tert-butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenyl]-3-hydroxy-pent-1-enyl}-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

There total 26 articles about Benzoic acid (3aR,4R,5R,6aS)-4-{(E)-(R)-5-[2-(tert-butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenyl]-3-hydroxy-pent-1-enyl}-2-oxo-hexahydro-cyclopenta[b]furan-5-yl 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:

Benzoic acid (3aR,5R,6aS)-4-formyl-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester (39746-01-5,61348-03-6,61348-04-7,98673-94-0,118711-80-1) → Benzoic acid (3aR,5R,6aS)-4-{(E)-(S)-5-[2-(tert-butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenyl]-3-hydroxy-pent-1-enyl}-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester (117625-51-1,117706-92-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / NaH

2: NaBH₄, CeCl₃ / methanol

With sodium tetrahydroborate; cerium(III) chloride; sodium hydride; In methanol;

DOI:10.1016/S0040-4039(00)95644-2

Reference yield:

Benzoic acid (3aR,5R,6aS)-4-formyl-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester (39746-01-5,61348-03-6,61348-04-7,98673-94-0,118711-80-1) → Benzoic acid (3aR,5R,6aS)-4-{(E)-(R)-5-[2-(tert-butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenyl]-3-hydroxy-pent-1-enyl}-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester (117625-51-1,117706-92-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / NaH

2: NaBH₄, CeCl₃ / methanol

With sodium tetrahydroborate; cerium(III) chloride; sodium hydride; In methanol;

DOI:10.1016/S0040-4039(00)95644-2

Reference yield:

3-(4-aminophenyl)propionic acid (2393-17-1) → Benzoic acid (3aR,5R,6aS)-4-{(E)-(S)-5-[2-(tert-butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenyl]-3-hydroxy-pent-1-enyl}-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester (117625-51-1,117706-92-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 90 percent / HCl, NaNO₂, NaN₃

2: 56 percent / TFA

3: 65 percent / 6 M HCl

4: 70 percent / pyridine

5: 90 percent / imidazole

6: 99 percent / n-BuLi

7: 71 percent / NaH

8: NaBH₄, CeCl₃ / methanol

With pyridine; 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; sodium azide; cerium(III) chloride; sodium hydride; trifluoroacetic acid; sodium nitrite; In methanol;

DOI:10.1016/S0040-4039(00)95644-2

upstream raw materials:

Benzoic acid (3aR,5R,6aS)-4-{(E)-5-[2-(tert-butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenyl]-3-oxo-pent-1-enyl}-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

Benzoic acid (3aR,5R,6aS)-4-formyl-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

3-(4-aminophenyl)propionic acid

3-(4-Amino-2-hydroxy-phenyl)-propionic acid methyl ester

Downstream raw materials:

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

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

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

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

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