(1S,7R,7aS)-7-Acetoxy-1-[(R)-3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-5-((1S,4S)-3,3-dimethyl-2-oxo-7-oxa-bicyclo[2.2.1]hept-1-ylmethyl)-1,7a-dimethyl-2,6,7,7a-tetrahydro-1H-indene-4-carboxylic acid methyl ester

Base Information

• Chemical Name: (1S,7R,7aS)-7-Acetoxy-1-[(R)-3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-5-((1S,4S)-3,3-dimethyl-2-oxo-7-oxa-bicyclo[2.2.1]hept-1-ylmethyl)-1,7a-dimethyl-2,6,7,7a-tetrahydro-1H-indene-4-carboxylic acid methyl ester
• CAS No.: 131041-22-0
• Molecular Formula: C₄₄H₅₈O₇Si
• Molecular Weight: 727.026

Synonyms:(1S,7R,7aS)-7-Acetoxy-1-[(R)-3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-5-((1S,4S)-3,3-dimethyl-2-oxo-7-oxa-bicyclo[2.2.1]hept-1-ylmethyl)-1,7a-dimethyl-2,6,7,7a-tetrahydro-1H-indene-4-carboxylic acid methyl ester

Chemical Property of (1S,7R,7aS)-7-Acetoxy-1-[(R)-3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-5-((1S,4S)-3,3-dimethyl-2-oxo-7-oxa-bicyclo[2.2.1]hept-1-ylmethyl)-1,7a-dimethyl-2,6,7,7a-tetrahydro-1H-indene-4-carboxylic acid methyl ester

Chemical Property:

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Technology Process of (1S,7R,7aS)-7-Acetoxy-1-[(R)-3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-5-((1S,4S)-3,3-dimethyl-2-oxo-7-oxa-bicyclo[2.2.1]hept-1-ylmethyl)-1,7a-dimethyl-2,6,7,7a-tetrahydro-1H-indene-4-carboxylic acid methyl ester

There total 12 articles about (1S,7R,7aS)-7-Acetoxy-1-[(R)-3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-5-((1S,4S)-3,3-dimethyl-2-oxo-7-oxa-bicyclo[2.2.1]hept-1-ylmethyl)-1,7a-dimethyl-2,6,7,7a-tetrahydro-1H-indene-4-carboxylic acid methyl 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: 83.0%

acetic anhydride (108-24-7) + (1aR,4aS,7S,7aS)-7-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-propyl]-3-((1S,4S)-3,3-dimethyl-2-oxo-7-oxa-bicyclo[2.2.1]hept-1-ylmethyl)-4a,7-dimethyl-1a,2,4a,5,6,7-hexahydro-1-oxa-cyclopropa[d]indene-4-carboxylic acid methyl ester (131041-21-9) → (1S,7R,7aS)-7-Acetoxy-1-[(R)-3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-5-((1S,4S)-3,3-dimethyl-2-oxo-7-oxa-bicyclo[2.2.1]hept-1-ylmethyl)-1,7a-dimethyl-2,6,7,7a-tetrahydro-1H-indene-4-carboxylic acid methyl ester (131041-22-0)

Guidance literature:

With iron(III) chloride; In dichloromethane; at -78 ℃; for 12h;

DOI:10.1021/ja00180a064

Reference yield:

2,2-dimethyl-1,3-cyclohexanedione (562-13-0) → (1S,7R,7aS)-7-Acetoxy-1-[(R)-3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-5-((1S,4S)-3,3-dimethyl-2-oxo-7-oxa-bicyclo[2.2.1]hept-1-ylmethyl)-1,7a-dimethyl-2,6,7,7a-tetrahydro-1H-indene-4-carboxylic acid methyl ester (131041-22-0)

Guidance literature:

Multi-step reaction with 12 steps

1: catechol borane, oxazaborolidine / toluene / -78 °C

2: imidazole / dimethylformamide / 23 °C

3: NaH, THF

4: 1.) NaH / 1.) THF, 23 deg C, 2.) -40 deg C

5: 66 percent / Pd(OAc)2, PPh₃ / tetrahydrofuran / 0.25 h / 70 °C

6: NaHB(OMe)3 / tetrahydrofuran / 8 h / -20 °C

7: pyridine / CH₂Cl₂ / 0.5 h / 23 °C

8: Cl₃CCOOH / tetrahydrofuran; H₂O / 5 h / 23 °C

9: 1.) a) mercuric trifluoroacetate, HgO, b) Et₄NCl, 2.) Bu₂SnH₂ / 1.) a) CH₃CN, 23 deg C, 24 h, 2.) toluene, from -78 deg C to 0 deg C

10: K₂CO₃-methanol / methanol / 0.17 h / 23 °C

11: pyridinium dichromate / dimethylformamide / 0.5 h / 23 °C

12: 83 percent / FeCl₃ / CH₂Cl₂ / 12 h / -78 °C

With tetrahydrofuran; pyridine; 1H-imidazole; methanol; palladium diacetate; dipyridinium dichromate; (S)-oxazaborolidine; tetraethylammonium chloride; mercury(II) trifluoroacetate; sodium trimethoxyborohydride; iron(III) chloride; sodium hydride; dibutyltin; potassium carbonate; triphenylphosphine; mercury(II) oxide; trichloroacetic acid; benzo[1,3,2]dioxaborole; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00180a064

Reference yield:

(S)-3-hydroxy-2,2-dimethylcyclohexanone (61447-86-7) → (1S,7R,7aS)-7-Acetoxy-1-[(R)-3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-5-((1S,4S)-3,3-dimethyl-2-oxo-7-oxa-bicyclo[2.2.1]hept-1-ylmethyl)-1,7a-dimethyl-2,6,7,7a-tetrahydro-1H-indene-4-carboxylic acid methyl ester (131041-22-0)

Guidance literature:

Multi-step reaction with 11 steps

1: imidazole / dimethylformamide / 23 °C

2: NaH, THF

3: 1.) NaH / 1.) THF, 23 deg C, 2.) -40 deg C

4: 66 percent / Pd(OAc)2, PPh₃ / tetrahydrofuran / 0.25 h / 70 °C

5: NaHB(OMe)3 / tetrahydrofuran / 8 h / -20 °C

6: pyridine / CH₂Cl₂ / 0.5 h / 23 °C

7: Cl₃CCOOH / tetrahydrofuran; H₂O / 5 h / 23 °C

8: 1.) a) mercuric trifluoroacetate, HgO, b) Et₄NCl, 2.) Bu₂SnH₂ / 1.) a) CH₃CN, 23 deg C, 24 h, 2.) toluene, from -78 deg C to 0 deg C

9: K₂CO₃-methanol / methanol / 0.17 h / 23 °C

10: pyridinium dichromate / dimethylformamide / 0.5 h / 23 °C

11: 83 percent / FeCl₃ / CH₂Cl₂ / 12 h / -78 °C

With tetrahydrofuran; pyridine; 1H-imidazole; methanol; palladium diacetate; dipyridinium dichromate; tetraethylammonium chloride; mercury(II) trifluoroacetate; sodium trimethoxyborohydride; iron(III) chloride; sodium hydride; dibutyltin; potassium carbonate; triphenylphosphine; mercury(II) oxide; trichloroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ja00180a064

upstream raw materials:

acetic anhydride

(1aR,4aS,7S,7aS)-7-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-propyl]-3-((1S,4S)-3,3-dimethyl-2-oxo-7-oxa-bicyclo[2.2.1]hept-1-ylmethyl)-4a,7-dimethyl-1a,2,4a,5,6,7-hexahydro-1-oxa-cyclopropa[d]indene-4-carboxylic acid methyl ester

2,2-dimethyl-1,3-cyclohexanedione

(S)-3-hydroxy-2,2-dimethylcyclohexanone

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