(3S,3aS,6R,7R,7aR)-3-(tert-Butyl-diphenyl-silanyloxy)-7-(2-methoxy-ethoxymethoxy)-octahydro-benzo[b]thiophene-6-carboxylic acid methyl ester

Base Information

• Chemical Name: (3S,3aS,6R,7R,7aR)-3-(tert-Butyl-diphenyl-silanyloxy)-7-(2-methoxy-ethoxymethoxy)-octahydro-benzo[b]thiophene-6-carboxylic acid methyl ester
• CAS No.: 144085-89-2
• Molecular Formula: C₃₀H₄₂O₆SSi
• Molecular Weight: 558.811
• Mol file: 144085-89-2.mol

Synonyms:(3S,3aS,6R,7R,7aR)-3-(tert-Butyl-diphenyl-silanyloxy)-7-(2-methoxy-ethoxymethoxy)-octahydro-benzo[b]thiophene-6-carboxylic acid methyl ester

Chemical Property of (3S,3aS,6R,7R,7aR)-3-(tert-Butyl-diphenyl-silanyloxy)-7-(2-methoxy-ethoxymethoxy)-octahydro-benzo[b]thiophene-6-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,3aS,6R,7R,7aR)-3-(tert-Butyl-diphenyl-silanyloxy)-7-(2-methoxy-ethoxymethoxy)-octahydro-benzo[b]thiophene-6-carboxylic acid methyl ester

There total 17 articles about (3S,3aS,6R,7R,7aR)-3-(tert-Butyl-diphenyl-silanyloxy)-7-(2-methoxy-ethoxymethoxy)-octahydro-benzo[b]thiophene-6-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: 94.0%

tert-butyldiphenylsilyl triflate (92886-86-7) + (3S,3aS,6R,7R,7aR)-3-Hydroxy-7-(2-methoxy-ethoxymethoxy)-octahydro-benzo[b]thiophene-6-carboxylic acid methyl ester (144085-80-3,144176-91-0) → (3S,3aS,6R,7R,7aR)-3-(tert-Butyl-diphenyl-silanyloxy)-7-(2-methoxy-ethoxymethoxy)-octahydro-benzo[b]thiophene-6-carboxylic acid methyl ester (144085-89-2)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; a) 0 deg C, 30 min, b) RT, 2 h;

Reference yield:

(1R,2R,5S,6S)-5-Acetyl-7-oxa-bicyclo[4.1.0]heptane-2-carboxylic acid methyl ester → (3S,3aS,6R,7R,7aR)-3-(tert-Butyl-diphenyl-silanyloxy)-7-(2-methoxy-ethoxymethoxy)-octahydro-benzo[b]thiophene-6-carboxylic acid methyl ester (144085-89-2)

Guidance literature:

Multi-step reaction with 12 steps

1: DBU / CH₂Cl₂; methanol

2: 1.) LDA, 2.) NCS / 1.) THF, hexane, -78 deg C, 2 h, 2.) THF, hexane, -78 deg C, 30 min

3: 84 percent / air / benzene / 5 h / Ambient temperature

4: 61 percent / NaOMe / methanol / 4 h / Ambient temperature

5: 84 percent / diisopropylethylamine, DMAP / CH₂Cl₂ / 48 h / Ambient temperature

6: 87 percent / NaBH₄ / methanol / 0.17 h / -20 °C

7: 7 percent / (+)-2-(phenylsulfonyl)-3-phenyloxaziridine / CH₂Cl₂ / 1.5 h / 0 °C

8: 53 percent / (dimethylamino)pyridine, Et₃N / CH₂Cl₂ / 0.08 h / Ambient temperature

9: 94 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / benzene / 3 h / Ambient temperature

10: 70 percent / NaI, trifluoroacetic anhydride / acetone / 0.08 h / 0 °C

11: 1.) BH₃*THF, 2.) 10percent NaOH, 30percent aq. H₂O₂ / 1.) THF, RT, 3 h, 2.) THF, 0.5 h

12: 94 percent / 2,6-lutidine / CH₂Cl₂ / a) 0 deg C, 30 min, b) RT, 2 h

With 2,6-dimethylpyridine; dmap; sodium hydroxide; sodium tetrahydroborate; N-chloro-succinimide; borane-THF; air; dihydrogen peroxide; sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; (+)-2-(phenylsulfonyl)-3-phenyloxaziridine; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; sodium iodide; lithium diisopropyl amide; In methanol; dichloromethane; acetone; benzene;

Reference yield:

(1S,2R)-4-Acetyl-2-hydroxy-cyclohex-3-enecarboxylic acid methyl ester (133816-92-9) → (3S,3aS,6R,7R,7aR)-3-(tert-Butyl-diphenyl-silanyloxy)-7-(2-methoxy-ethoxymethoxy)-octahydro-benzo[b]thiophene-6-carboxylic acid methyl ester (144085-89-2)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) LDA, 2.) NCS / 1.) THF, hexane, -78 deg C, 2 h, 2.) THF, hexane, -78 deg C, 30 min

2: 84 percent / air / benzene / 5 h / Ambient temperature

3: 61 percent / NaOMe / methanol / 4 h / Ambient temperature

4: 84 percent / diisopropylethylamine, DMAP / CH₂Cl₂ / 48 h / Ambient temperature

5: 87 percent / NaBH₄ / methanol / 0.17 h / -20 °C

6: 7 percent / (+)-2-(phenylsulfonyl)-3-phenyloxaziridine / CH₂Cl₂ / 1.5 h / 0 °C

7: 53 percent / (dimethylamino)pyridine, Et₃N / CH₂Cl₂ / 0.08 h / Ambient temperature

8: 94 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / benzene / 3 h / Ambient temperature

9: 70 percent / NaI, trifluoroacetic anhydride / acetone / 0.08 h / 0 °C

10: 1.) BH₃*THF, 2.) 10percent NaOH, 30percent aq. H₂O₂ / 1.) THF, RT, 3 h, 2.) THF, 0.5 h

11: 94 percent / 2,6-lutidine / CH₂Cl₂ / a) 0 deg C, 30 min, b) RT, 2 h

With 2,6-dimethylpyridine; dmap; sodium hydroxide; sodium tetrahydroborate; N-chloro-succinimide; borane-THF; air; dihydrogen peroxide; sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; (+)-2-(phenylsulfonyl)-3-phenyloxaziridine; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; sodium iodide; lithium diisopropyl amide; In methanol; dichloromethane; acetone; benzene;

upstream raw materials:

tert-butyldiphenylsilyl triflate

(3S,3aS,6R,7R,7aR)-3-Hydroxy-7-(2-methoxy-ethoxymethoxy)-octahydro-benzo[b]thiophene-6-carboxylic acid methyl ester

(1S,2R)-4-Acetyl-2-hydroxy-cyclohex-3-enecarboxylic acid methyl ester

(3aR,6S,7S,7aS)-7-Hydroxy-3-oxo-octahydro-benzo[b]thiophene-6-carboxylic acid methyl ester

Downstream raw materials:

(3S,3aS,6R,7R,7aR)-3-(tert-Butyl-diphenyl-silanyloxy)-7-(2-methoxy-ethoxymethoxy)-octahydro-benzo[b]thiophene-6-carbaldehyde

6-[(3S,3aS,6R,7R,7aR)-3-(tert-Butyl-diphenyl-silanyloxy)-7-(2-methoxy-ethoxymethoxy)-octahydro-benzo[b]thiophene-6-carbonyl]-3-methyl-2,3-dihydro-pyran-4-one

C₃₁H₄₀O₅SSi

6-[(3S,3aS,6R,7R,7aR)-3-(tert-Butyl-diphenyl-silanyloxy)-7-hydroxy-octahydro-benzo[b]thiophene-6-carbonyl]-3-methyl-2,3-dihydro-pyran-4-one