(4aS,6S,8aR)-6-(tert-Butyl-diphenyl-silanyloxy)-8a-(2-trimethylsilanyl-ethoxymethoxymethyl)-3,4,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

Base Information

• Chemical Name: (4aS,6S,8aR)-6-(tert-Butyl-diphenyl-silanyloxy)-8a-(2-trimethylsilanyl-ethoxymethoxymethyl)-3,4,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester
• CAS No.: 615249-10-0
• Molecular Formula: C₃₅H₅₂O₅Si₂
• Molecular Weight: 608.966

Synonyms:(4aS,6S,8aR)-6-(tert-Butyl-diphenyl-silanyloxy)-8a-(2-trimethylsilanyl-ethoxymethoxymethyl)-3,4,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

Chemical Property of (4aS,6S,8aR)-6-(tert-Butyl-diphenyl-silanyloxy)-8a-(2-trimethylsilanyl-ethoxymethoxymethyl)-3,4,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aS,6S,8aR)-6-(tert-Butyl-diphenyl-silanyloxy)-8a-(2-trimethylsilanyl-ethoxymethoxymethyl)-3,4,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

There total 7 articles about (4aS,6S,8aR)-6-(tert-Butyl-diphenyl-silanyloxy)-8a-(2-trimethylsilanyl-ethoxymethoxymethyl)-3,4,4a,5,6,7,8,8a-octahydro-naphthalene-1-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: 89.0%

methanol (67-56-1) + carbon monoxide (201230-82-2) + Trifluoro-methanesulfonic acid (4aS,6S,8aS)-6-(tert-butyl-diphenyl-silanyloxy)-8a-(2-trimethylsilanyl-ethoxymethoxymethyl)-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl ester (615249-30-4) → (4aS,6S,8aR)-6-(tert-Butyl-diphenyl-silanyloxy)-8a-(2-trimethylsilanyl-ethoxymethoxymethyl)-3,4,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester (615249-10-0)

Guidance literature:

With palladium diacetate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In N,N-dimethyl-formamide; at 60 ℃; for 12h; under 760 Torr;

DOI:10.1002/anie.200351744

Reference yield:

(S)-3,4,8,8a-tetrahydro-8a-(hydroxymethyl)-1,6-(2H,7H)-naphthalenedione-1-ethylene acetal (98770-78-6) → (4aS,6S,8aR)-6-(tert-Butyl-diphenyl-silanyloxy)-8a-(2-trimethylsilanyl-ethoxymethoxymethyl)-3,4,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester (615249-10-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 85 percent / i-Pr₂NEt / CH₂Cl₂ / 20 h / 25 °C

2: 80 percent / Li; liq. NH₃ / 1 h / -78 °C

3: 99 percent / NaBH₄ / tetrahydrofuran; ethanol / 3 h / -78 - 25 °C

4: 80 percent / imidazole; DMAP / dimethylformamide / 24 h / 25 °C

5: PPTS / acetone / 24 h / 65 °C

6: KHMDS / tetrahydrofuran / 0.5 h / -78 °C

7: 89 percent / PPh₃; Pd(OAc)2; i-Pr₂NEt / dimethylformamide / 12 h / 60 °C / 760 Torr

With 1H-imidazole; dmap; palladium diacetate; sodium tetrahydroborate; ammonia; pyridinium p-toluenesulfonate; lithium; potassium hexamethylsilazane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; 2: Birch reduction;

DOI:10.1002/anie.200351744

Reference yield:

C19H32O5Si (615249-06-4) → (4aS,6S,8aR)-6-(tert-Butyl-diphenyl-silanyloxy)-8a-(2-trimethylsilanyl-ethoxymethoxymethyl)-3,4,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester (615249-10-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 80 percent / Li; liq. NH₃ / 1 h / -78 °C

2: 99 percent / NaBH₄ / tetrahydrofuran; ethanol / 3 h / -78 - 25 °C

3: 80 percent / imidazole; DMAP / dimethylformamide / 24 h / 25 °C

4: PPTS / acetone / 24 h / 65 °C

5: KHMDS / tetrahydrofuran / 0.5 h / -78 °C

6: 89 percent / PPh₃; Pd(OAc)2; i-Pr₂NEt / dimethylformamide / 12 h / 60 °C / 760 Torr

With 1H-imidazole; dmap; palladium diacetate; sodium tetrahydroborate; ammonia; pyridinium p-toluenesulfonate; lithium; potassium hexamethylsilazane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; acetone; 1: Birch reduction;

DOI:10.1002/anie.200351744

upstream raw materials:

methanol

carbon monoxide

Trifluoro-methanesulfonic acid (4aS,6S,8aS)-6-(tert-butyl-diphenyl-silanyloxy)-8a-(2-trimethylsilanyl-ethoxymethoxymethyl)-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl ester

(S)-3,4,8,8a-tetrahydro-8a-(hydroxymethyl)-1,6-(2H,7H)-naphthalenedione-1-ethylene acetal

Downstream raw materials:

Acetic acid (3aR,4S,6aR,8S,10aR)-4-methyl-3,5-dioxo-4-((1R,2R,4S,6R)-3-oxo-6-phenyl-bicyclo[2.2.1]hept-2-yl)-decahydro-2-oxa-cyclopenta[d]naphthalen-8-yl ester

C₂₉H₃₄O₆

C₂₈H₃₁BrO₇

C₂₉H₃₈O₇

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