(3aR,4R,7aS)-4-(tert-Butyl-diphenyl-silanyloxy)-7a-methyl-1-oxo-octahydro-indene-2-carboxylic acid methyl ester

Base Information

Chemical Name:(3aR,4R,7aS)-4-(tert-Butyl-diphenyl-silanyloxy)-7a-methyl-1-oxo-octahydro-indene-2-carboxylic acid methyl ester
CAS No.:312584-28-4
Molecular Formula:C₂₈H₃₆O₄Si
Molecular Weight:464.677
Hs Code.:

Synonyms:(3aR,4R,7aS)-4-(tert-Butyl-diphenyl-silanyloxy)-7a-methyl-1-oxo-octahydro-indene-2-carboxylic acid methyl ester

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Chemical Property of (3aR,4R,7aS)-4-(tert-Butyl-diphenyl-silanyloxy)-7a-methyl-1-oxo-octahydro-indene-2-carboxylic acid methyl ester

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Technology Process of (3aR,4R,7aS)-4-(tert-Butyl-diphenyl-silanyloxy)-7a-methyl-1-oxo-octahydro-indene-2-carboxylic acid methyl ester

There total 14 articles about (3aR,4R,7aS)-4-(tert-Butyl-diphenyl-silanyloxy)-7a-methyl-1-oxo-octahydro-indene-2-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: 99.0%

: 312584-32-0
(1S,2R,3R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(2-methoxycarbonyl-ethyl)-1-methyl-cyclohexanecarboxylic acid methyl ester

: 312584-28-4
(3aR,4R,7aS)-4-(tert-Butyl-diphenyl-silanyloxy)-7a-methyl-1-oxo-octahydro-indene-2-carboxylic acid methyl ester

Guidance literature:: With sodium hexamethyldisilazane; In tetrahydrofuran; at 0 - 20 ℃; for 12h;
DOI:10.1002/1099-0690(200010)2000:20<3427::aid-ejoc3427>3.3.co;2-o

Reference yield:

: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

: 312584-28-4
(3aR,4R,7aS)-4-(tert-Butyl-diphenyl-silanyloxy)-7a-methyl-1-oxo-octahydro-indene-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 14 steps

1.1: 4.53 g / p-TsOH / acetic acid / 5 h / 20 °C

2.1: 5.33 g / p-TsOH / toluene / 12 h / Heating; Dean-Stark apparatus

3.1: Na; liq. NH₃ / 1 h

4.1: BH₃*THF / 15 h / 0 - 20 °C

4.2: 83 percent / NaOH (3N); H₂O₂ (30 percent) / tetrahydrofuran / 4 h

5.1: 96 percent / mol. sieves; NMO; TPAP / CH₂Cl₂ / 3 h / 20 °C

6.1: 85 percent / NaOMe / methanol / 24 h / 20 °C

7.1: Li; liq. NH₃ / methanol / 2 h / -78 °C

8.1: p-TsOH; H₂O; Me₂CO / 10 h / 20 °C

9.1: 98 percent / imidazole / dimethylformamide / 48 h / 20 °C

10.1: Et₃N; NaI / acetonitrile / 12 h / 20 °C

11.1: mCPBA (70 percent) / pentane / 0.42 h / 0 °C

11.2: HCl (12N) / methanol / 0.08 h / 0 °C

12.1: Pb(OAc)4 / CH₂Cl₂ / 0.5 h / 0 °C

13.1: 85 percent / ozone / CH₂Cl₂ / -78 °C

14.1: 99 percent / NaHMDS / tetrahydrofuran / 12 h / 0 - 20 °C

With 1H-imidazole; lead(IV) acetate; N-methyl-2-indolinone; molecular sieve; tetrapropylammonium perruthennate; borane-THF; ammonia; water; sodium methylate; sodium hexamethyldisilazane; sodium; lithium; toluene-4-sulfonic acid; ozone; triethylamine; 3-chloro-benzenecarboperoxoic acid; acetone; sodium iodide; In tetrahydrofuran; methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; toluene; acetonitrile; pentane; 1.1: Cyclization / 2.1: Etherification / 3.1: Reduction / 4.1: Addition / 4.2: Oxidation / 5.1: Oxidation / 6.1: Isomerization / 7.1: Reduction / 8.1: Hydrolysis / 9.1: Substitution / 10.1: Substitution / 11.1: Oxidation / 11.2: Hydrolysis / 12.1: Ring cleavage / 13.1: Oxidation / 14.1: Cyclization;
DOI:10.1002/1099-0690(200010)2000:20<3427::aid-ejoc3427>3.3.co;2-o

Reference yield:

: 145632-33-3
(S)-7a′-methyl-2′,3′,7′,7a′-tetrahydrospiro[[1,3]dithiolane-2,5′-inden]-1′(6′H)-one

: 312584-28-4
(3aR,4R,7aS)-4-(tert-Butyl-diphenyl-silanyloxy)-7a-methyl-1-oxo-octahydro-indene-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: 5.33 g / p-TsOH / toluene / 12 h / Heating; Dean-Stark apparatus

2.1: Na; liq. NH₃ / 1 h

3.1: BH₃*THF / 15 h / 0 - 20 °C

3.2: 83 percent / NaOH (3N); H₂O₂ (30 percent) / tetrahydrofuran / 4 h

4.1: 96 percent / mol. sieves; NMO; TPAP / CH₂Cl₂ / 3 h / 20 °C

5.1: 85 percent / NaOMe / methanol / 24 h / 20 °C

6.1: Li; liq. NH₃ / methanol / 2 h / -78 °C

7.1: p-TsOH; H₂O; Me₂CO / 10 h / 20 °C

8.1: 98 percent / imidazole / dimethylformamide / 48 h / 20 °C

9.1: Et₃N; NaI / acetonitrile / 12 h / 20 °C

10.1: mCPBA (70 percent) / pentane / 0.42 h / 0 °C

10.2: HCl (12N) / methanol / 0.08 h / 0 °C

11.1: Pb(OAc)4 / CH₂Cl₂ / 0.5 h / 0 °C

12.1: 85 percent / ozone / CH₂Cl₂ / -78 °C

13.1: 99 percent / NaHMDS / tetrahydrofuran / 12 h / 0 - 20 °C

With 1H-imidazole; lead(IV) acetate; N-methyl-2-indolinone; molecular sieve; tetrapropylammonium perruthennate; borane-THF; ammonia; water; sodium methylate; sodium hexamethyldisilazane; sodium; lithium; toluene-4-sulfonic acid; ozone; triethylamine; 3-chloro-benzenecarboperoxoic acid; acetone; sodium iodide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; pentane; 1.1: Etherification / 2.1: Reduction / 3.1: Addition / 3.2: Oxidation / 4.1: Oxidation / 5.1: Isomerization / 6.1: Reduction / 7.1: Hydrolysis / 8.1: Substitution / 9.1: Substitution / 10.1: Oxidation / 10.2: Hydrolysis / 11.1: Ring cleavage / 12.1: Oxidation / 13.1: Cyclization;
DOI:10.1002/1099-0690(200010)2000:20<3427::aid-ejoc3427>3.3.co;2-o