Benzoic acid (E)-(5R,7R,9R)-5,7-dihydroxy-10-(4-methoxy-benzyloxy)-9-methyl-dec-3-enyl ester

Base Information

• Chemical Name: Benzoic acid (E)-(5R,7R,9R)-5,7-dihydroxy-10-(4-methoxy-benzyloxy)-9-methyl-dec-3-enyl ester
• CAS No.: 856410-44-1
• Molecular Formula: C₂₆H₃₄O₆
• Molecular Weight: 442.552
• Mol file: 856410-44-1.mol

Synonyms:Benzoic acid (E)-(5R,7R,9R)-5,7-dihydroxy-10-(4-methoxy-benzyloxy)-9-methyl-dec-3-enyl ester

Chemical Property of Benzoic acid (E)-(5R,7R,9R)-5,7-dihydroxy-10-(4-methoxy-benzyloxy)-9-methyl-dec-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (E)-(5R,7R,9R)-5,7-dihydroxy-10-(4-methoxy-benzyloxy)-9-methyl-dec-3-enyl ester

There total 6 articles about Benzoic acid (E)-(5R,7R,9R)-5,7-dihydroxy-10-(4-methoxy-benzyloxy)-9-methyl-dec-3-enyl 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: 85.0%

Benzoic acid (E)-(5R,7R,9R)-7-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-10-(4-methoxy-benzyloxy)-9-methyl-dec-3-enyl ester (856410-63-4) → Benzoic acid (E)-(5R,7R,9R)-5,7-dihydroxy-10-(4-methoxy-benzyloxy)-9-methyl-dec-3-enyl ester (856410-44-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

DOI:10.1002/anie.200500029

Reference yield:

tert-Butyl-{(S)-1-[(R)-3-(4-methoxy-benzyloxy)-2-methyl-propyl]-but-3-enyloxy}-dimethyl-silane (856410-60-1) → Benzoic acid (E)-(5R,7R,9R)-5,7-dihydroxy-10-(4-methoxy-benzyloxy)-9-methyl-dec-3-enyl ester (856410-44-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: OsO₄; NMO / tetrahydrofuran; H₂O / 20 °C

1.2: NaIO₄ / tetrahydrofuran; H₂O

1.3: 75 percent / NiCl₂; CrCl₂ / dimethylsulfoxide / 20 °C

2.1: 91 percent / Dess-Martin periodinane

3.1: 99 percent / BH₃*THF; (S)-Corey-Bakshi-Shibata oxazaborolidine reagent / tetrahydrofuran / -40 °C

4.1: 85 percent / TBAF / tetrahydrofuran / 20 °C

With osmium(VIII) oxide; N-methyl-2-indolinone; borane-THF; (S)-Corey-Bakshi-Shibata oxazaborolidine reagent; tetrabutyl ammonium fluoride; Dess-Martin periodane; In tetrahydrofuran; water; 2.1: Dess-Martin oxidation;

DOI:10.1002/anie.200500029

Reference yield:

Benzoic acid (E)-(7R,9R)-7-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-9-methyl-5-oxo-dec-3-enyl ester (856410-62-3) → Benzoic acid (E)-(5R,7R,9R)-5,7-dihydroxy-10-(4-methoxy-benzyloxy)-9-methyl-dec-3-enyl ester (856410-44-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / BH₃*THF; (S)-Corey-Bakshi-Shibata oxazaborolidine reagent / tetrahydrofuran / -40 °C

2: 85 percent / TBAF / tetrahydrofuran / 20 °C

With borane-THF; (S)-Corey-Bakshi-Shibata oxazaborolidine reagent; tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1002/anie.200500029

upstream raw materials:

Benzoic acid (E)-(5R,7R,9R)-7-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-10-(4-methoxy-benzyloxy)-9-methyl-dec-3-enyl ester

tert-Butyl-{(S)-1-[(R)-3-(4-methoxy-benzyloxy)-2-methyl-propyl]-but-3-enyloxy}-dimethyl-silane

Benzoic acid (E)-(7R,9R)-7-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-10-(4-methoxy-benzyloxy)-9-methyl-dec-3-enyl ester

Benzoic acid (E)-(7R,9R)-7-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-9-methyl-5-oxo-dec-3-enyl ester

Downstream raw materials:

(2R,6S)-2-{(2R)-6-[3-(4-methoxybenzyloxy)-2-methylpropyl]-5,6-dihydro-2H-pyran-2-yl}-ethanol

{(2R)-6-[3-(4-methoxybenzyloxy)-2-methyl-propyl]-(2R,6S)-5,6-dihydro-2H-pyran-2-yl}acetaldehyde

laulimalide

C₆₆H₉₈O₈Si₃