Benzoic acid 2-{(2R,6S)-6-[(R)-3-(4-methoxy-benzyloxy)-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-ethyl ester

Base Information

• Chemical Name: Benzoic acid 2-{(2R,6S)-6-[(R)-3-(4-methoxy-benzyloxy)-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-ethyl ester
• CAS No.: 856410-45-2
• Molecular Formula: C₂₆H₃₂O₅
• Molecular Weight: 424.537

Synonyms:Benzoic acid 2-{(2R,6S)-6-[(R)-3-(4-methoxy-benzyloxy)-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-ethyl ester

Chemical Property of Benzoic acid 2-{(2R,6S)-6-[(R)-3-(4-methoxy-benzyloxy)-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of Benzoic acid 2-{(2R,6S)-6-[(R)-3-(4-methoxy-benzyloxy)-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-ethyl ester

There total 6 articles about Benzoic acid 2-{(2R,6S)-6-[(R)-3-(4-methoxy-benzyloxy)-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-ethyl 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 (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 2-{(2R,6S)-6-[(R)-3-(4-methoxy-benzyloxy)-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-ethyl ester (856410-45-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 99 percent / BH₃*THF; (S)-Corey-Bakshi-Shibata oxazaborolidine reagent / tetrahydrofuran / -40 °C

2.1: 85 percent / TBAF / tetrahydrofuran / 20 °C

3.1: PdCl₂(CH₃CN)2 / tetrahydrofuran / 1 h / -5 °C

3.2: 60 percent / benzoquinone / tetrahydrofuran / 48 h / 20 °C

With borane-THF; (S)-Corey-Bakshi-Shibata oxazaborolidine reagent; tetrabutyl ammonium fluoride; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran;

DOI:10.1002/anie.200500029

Reference yield:

(4S,6R)-7-(p-methoxybenzyloxy)-6-methylhept-1-en-4-ol (259198-98-6) → Benzoic acid 2-{(2R,6S)-6-[(R)-3-(4-methoxy-benzyloxy)-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-ethyl ester (856410-45-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 97 percent / imidazole / dimethylformamide / 20 °C

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

2.2: NaIO₄ / tetrahydrofuran; H₂O

2.3: 75 percent / NiCl₂; CrCl₂ / dimethylsulfoxide / 20 °C

3.1: 91 percent / Dess-Martin periodinane

4.1: 99 percent / BH₃*THF; (S)-Corey-Bakshi-Shibata oxazaborolidine reagent / tetrahydrofuran / -40 °C

5.1: 85 percent / TBAF / tetrahydrofuran / 20 °C

6.1: PdCl₂(CH₃CN)2 / tetrahydrofuran / 1 h / -5 °C

6.2: 60 percent / benzoquinone / tetrahydrofuran / 48 h / 20 °C

With 1H-imidazole; osmium(VIII) oxide; N-methyl-2-indolinone; borane-THF; (S)-Corey-Bakshi-Shibata oxazaborolidine reagent; tetrabutyl ammonium fluoride; Dess-Martin periodane; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; water; N,N-dimethyl-formamide; 3.1: Dess-Martin oxidation;

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 2-{(2R,6S)-6-[(R)-3-(4-methoxy-benzyloxy)-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-ethyl ester (856410-45-2)

Guidance literature:

Multi-step reaction with 5 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

5.1: PdCl₂(CH₃CN)2 / tetrahydrofuran / 1 h / -5 °C

5.2: 60 percent / benzoquinone / tetrahydrofuran / 48 h / 20 °C

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

DOI:10.1002/anie.200500029

upstream raw materials:

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

Benzoic acid (E)-(5R,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)-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

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