2,2-Dimethyl-propionic acid (E)-(S)-1-[(1S,3R,4S)-3-benzyloxy-1-(2-benzyloxy-ethyl)-4-methoxy-4-methyl-7-oxo-heptyl]-3-methyl-7-oxo-oct-3-enyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (E)-(S)-1-[(1S,3R,4S)-3-benzyloxy-1-(2-benzyloxy-ethyl)-4-methoxy-4-methyl-7-oxo-heptyl]-3-methyl-7-oxo-oct-3-enyl ester
• CAS No.: 130014-87-8
• Molecular Formula: C₃₉H₅₆O₇
• Molecular Weight: 636.869

Synonyms:

Chemical Property of 2,2-Dimethyl-propionic acid (E)-(S)-1-[(1S,3R,4S)-3-benzyloxy-1-(2-benzyloxy-ethyl)-4-methoxy-4-methyl-7-oxo-heptyl]-3-methyl-7-oxo-oct-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (E)-(S)-1-[(1S,3R,4S)-3-benzyloxy-1-(2-benzyloxy-ethyl)-4-methoxy-4-methyl-7-oxo-heptyl]-3-methyl-7-oxo-oct-3-enyl ester

There total 38 articles about 2,2-Dimethyl-propionic acid (E)-(S)-1-[(1S,3R,4S)-3-benzyloxy-1-(2-benzyloxy-ethyl)-4-methoxy-4-methyl-7-oxo-heptyl]-3-methyl-7-oxo-oct-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:

(1R,4S,5S,6S)-6-Benzyloxy-4-(3-hydroxy-propyl)-4-methyl-3-oxa-bicyclo[3.2.1]octan-2-one (130014-77-6) → 2,2-Dimethyl-propionic acid (E)-(S)-1-[(1S,3R,4S)-3-benzyloxy-1-(2-benzyloxy-ethyl)-4-methoxy-4-methyl-7-oxo-heptyl]-3-methyl-7-oxo-oct-3-enyl ester (130014-87-8,130143-27-0)

Guidance literature:

Multi-step reaction with 19 steps

1: (i-Pr)2NEt

2: LiAlH₄ / 0 °C

3: imidazole / dimethylformamide

4: NaH / dimethylformamide

5: H₂ / 10percent Pd/C / ethyl acetate

6: Swern oxidation

7: m-CPBA, Na₂HPO₄ / CH₂Cl₂

8: LiAlH₄ / 0 deg C to r.t.

9: NaH, (n-Bu)4NI / dimethylformamide

10: aq. AcOH / tetrahydrofuran / 55 °C

11: Swern oxidation

12: 18-crown-6, KCN

13: 1) LDA

14: 95 percent / (n-Bu)4NF / tetrahydrofuran / 0.17 h

15: LiAlH₄ / -78 deg C to r.t.

16: Et₃N / tetrahydrofuran / Heating

17: (n-Bu)4NF / hexamethylphosphoric acid triamide / 105 °C

18: 5percent HCl / tetrahydrofuran

19: Swern oxidation

With 1H-imidazole; hydrogenchloride; potassium cyanide; disodium hydrogenphosphate; lithium aluminium tetrahydride; 18-crown-6 ether; tetrabutyl ammonium fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)97370-2

Reference yield:

(1R,4S,5S,6S)-6-Benzyloxy-4-(3-hydroxy-propyl)-4-methyl-3-oxa-bicyclo[3.2.1]octan-2-one (130014-77-6) → 2,2-Dimethyl-propionic acid (E)-(R)-1-[(1S,3R,4S)-3-benzyloxy-1-(2-benzyloxy-ethyl)-4-methoxy-4-methyl-7-oxo-heptyl]-3-methyl-7-oxo-oct-3-enyl ester (130014-87-8,130143-27-0)

Guidance literature:

Multi-step reaction with 19 steps

1: (i-Pr)2NEt

2: LiAlH₄ / 0 °C

3: imidazole / dimethylformamide

4: NaH / dimethylformamide

5: H₂ / 10percent Pd/C / ethyl acetate

6: Swern oxidation

7: m-CPBA, Na₂HPO₄ / CH₂Cl₂

8: LiAlH₄ / 0 deg C to r.t.

9: NaH, (n-Bu)4NI / dimethylformamide

10: aq. AcOH / tetrahydrofuran / 55 °C

11: Swern oxidation

12: 18-crown-6, KCN

13: 1) LDA

14: 95 percent / (n-Bu)4NF / tetrahydrofuran / 0.17 h

15: LiAlH₄ / -78 deg C to r.t.

16: Et₃N / tetrahydrofuran / Heating

17: (n-Bu)4NF / hexamethylphosphoric acid triamide / 105 °C

18: 5percent HCl / tetrahydrofuran

19: Swern oxidation

With 1H-imidazole; hydrogenchloride; potassium cyanide; disodium hydrogenphosphate; lithium aluminium tetrahydride; 18-crown-6 ether; tetrabutyl ammonium fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)97370-2

Reference yield:

(R)-2-((1R,2R,4S)-2-Benzyloxy-4-hydroxymethyl-cyclopentyl)-5-(2-trimethylsilanyl-ethoxymethoxy)-pentan-2-ol (130014-78-7) → 2,2-Dimethyl-propionic acid (E)-(R)-1-[(1S,3R,4S)-3-benzyloxy-1-(2-benzyloxy-ethyl)-4-methoxy-4-methyl-7-oxo-heptyl]-3-methyl-7-oxo-oct-3-enyl ester (130014-87-8,130143-27-0)

Guidance literature:

Multi-step reaction with 17 steps

1: imidazole / dimethylformamide

2: NaH / dimethylformamide

3: H₂ / 10percent Pd/C / ethyl acetate

4: Swern oxidation

5: m-CPBA, Na₂HPO₄ / CH₂Cl₂

6: LiAlH₄ / 0 deg C to r.t.

7: NaH, (n-Bu)4NI / dimethylformamide

8: aq. AcOH / tetrahydrofuran / 55 °C

9: Swern oxidation

10: 18-crown-6, KCN

11: 1) LDA

12: 95 percent / (n-Bu)4NF / tetrahydrofuran / 0.17 h

13: LiAlH₄ / -78 deg C to r.t.

14: Et₃N / tetrahydrofuran / Heating

15: (n-Bu)4NF / hexamethylphosphoric acid triamide / 105 °C

16: 5percent HCl / tetrahydrofuran

17: Swern oxidation

With 1H-imidazole; hydrogenchloride; potassium cyanide; disodium hydrogenphosphate; lithium aluminium tetrahydride; 18-crown-6 ether; tetrabutyl ammonium fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)97370-2

upstream raw materials:

(1R,4S,5S,6S)-6-Benzyloxy-4-(3-hydroxy-propyl)-4-methyl-3-oxa-bicyclo[3.2.1]octan-2-one

(3R,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-6-methoxy-6-methyl-9-(2-trimethylsilanyl-ethoxymethoxy)-nonane-1,5-diol

(1R,2R,4S)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-2-[(R)-1-methoxy-1-methyl-4-(2-trimethylsilanyl-ethoxymethoxy)-butyl]-cyclopentanol

(2S,4S)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-2-[(R)-1-methoxy-1-methyl-4-(2-trimethylsilanyl-ethoxymethoxy)-butyl]-cyclopentanone

Downstream raw materials:

2,2-Dimethyl-propionic acid (3E,7Z)-(1S,11R,12S,14R)-12-benzyloxy-14-(2-benzyloxy-ethyl)-11-methoxy-3,7,11-trimethyl-cyclotetradeca-3,7-dienyl ester

2,2-Dimethyl-propionic acid (3E,7E)-(1S,11R,12S,14R)-12-benzyloxy-14-(2-benzyloxy-ethyl)-11-methoxy-3,7,11-trimethyl-cyclotetradeca-3,7-dienyl ester

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