1-[(3R,5S,5aR,9aR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4,4-dioxo-octahydro-4λ⁶-thia-3a-aza-cyclopenta[c]inden-5-yl]-octan-2-one

Base Information

• Chemical Name: 1-[(3R,5S,5aR,9aR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4,4-dioxo-octahydro-4λ⁶-thia-3a-aza-cyclopenta[c]inden-5-yl]-octan-2-one
• CAS No.: 780820-89-5
• Molecular Formula: C₃₅H₅₁NO₄SSi
• Molecular Weight: 609.946

Synonyms:1-[(3R,5S,5aR,9aR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4,4-dioxo-octahydro-4λ⁶-thia-3a-aza-cyclopenta[c]inden-5-yl]-octan-2-one

Chemical Property of 1-[(3R,5S,5aR,9aR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4,4-dioxo-octahydro-4λ⁶-thia-3a-aza-cyclopenta[c]inden-5-yl]-octan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(3R,5S,5aR,9aR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4,4-dioxo-octahydro-4λ⁶-thia-3a-aza-cyclopenta[c]inden-5-yl]-octan-2-one

There total 11 articles about 1-[(3R,5S,5aR,9aR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4,4-dioxo-octahydro-4λ⁶-thia-3a-aza-cyclopenta[c]inden-5-yl]-octan-2-one 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:

3-(tert-butyl-diphenyl-silanyloxymethyl)-octahydro-4-thia-3a-aza-cyclopenta[c]indene 4,4-dioxide (780820-85-1) → 1-[(3R,5S,5aR,9aR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4,4-dioxo-octahydro-4λ6-thia-3a-aza-cyclopenta[c]inden-5-yl]-octan-2-one (780820-89-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: t-BuLi / pentane; tetrahydrofuran / 0.25 h / -78 °C

1.2: BF₃*Et₂O / pentane; tetrahydrofuran / 3 h / -78 - 0 °C

2.1: 381 mg / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

With tert.-butyl lithium; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; pentane;

DOI:10.1016/j.tet.2006.01.111

Reference yield:

(D)-(-)-methyl homotyrosinate (477289-51-3) → 1-[(3R,5S,5aR,9aR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4,4-dioxo-octahydro-4λ6-thia-3a-aza-cyclopenta[c]inden-5-yl]-octan-2-one (780820-89-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 1.66 g / NEt₃ / CH₂Cl₂ / 4 h / 20 °C

2.1: 94 percent / NaBH₄ / ethanol; tetrahydrofuran / 0 - 20 °C

3.1: 90 percent / aq. NaOH / dioxane / 80 °C

4.1: PhI(OAc)2 / various solvent(s) / 0.5 h / 20 °C

5.1: 1.56 g / imidazole / dimethylformamide / 3 h / 20 °C

6.1: potassium hexamethyldisilazide / tetrahydrofuran / 8 h / -100 - 0 °C

6.2: BF₃*Et₂O; thiophenol / CH₂Cl₂ / 0 - 20 °C

6.3: 623 mg / Raney nickel / ethyl acetate; ethanol / 4 h / 20 °C

7.1: t-BuLi / tetrahydrofuran / 0.25 h / -78 °C

7.2: BF₃*Et₂O / tetrahydrofuran / 3 h / -78 - 0 °C

8.1: 381 g / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

With 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; [bis(acetoxy)iodo]benzene; tert.-butyl lithium; potassium hexamethylsilazane; Dess-Martin periodane; triethylamine; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/anie.200460178

Reference yield:

(R)-2-Hydroxymethyl-1-methanesulfonyl-1-aza-spiro[4.5]deca-6,9-dien-8-one (780820-77-1) → 1-[(3R,5S,5aR,9aR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4,4-dioxo-octahydro-4λ6-thia-3a-aza-cyclopenta[c]inden-5-yl]-octan-2-one (780820-89-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1.56 g / imidazole / dimethylformamide / 3 h / 20 °C

2.1: potassium hexamethyldisilazide / tetrahydrofuran / 8 h / -100 - 0 °C

2.2: BF₃*Et₂O; thiophenol / CH₂Cl₂ / 0 - 20 °C

2.3: 623 mg / Raney nickel / ethyl acetate; ethanol / 4 h / 20 °C

3.1: t-BuLi / tetrahydrofuran / 0.25 h / -78 °C

3.2: BF₃*Et₂O / tetrahydrofuran / 3 h / -78 - 0 °C

4.1: 381 g / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

With 1H-imidazole; tert.-butyl lithium; potassium hexamethylsilazane; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/anie.200460178

upstream raw materials:

3-(tert-butyl-diphenyl-silanyloxymethyl)-octahydro-4-thia-3a-aza-cyclopenta[c]indene 4,4-dioxide

1,2-Epoxyoctane

(D)-(-)-methyl homotyrosinate

(R)-2-Hydroxymethyl-1-methanesulfonyl-1-aza-spiro[4.5]deca-6,9-dien-8-one

Downstream raw materials:

(S)-1-[(2R,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-1-aza-spiro[4.5]dec-6-yl]-1-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-nonan-3-one

(3R,5R,7aR,11aR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hexyl-octahydro-pyrrolo[2,1-j]quinolin-7-one

(3R,5S,7aR,11aR)-3-[[(tert-butyldiphenylsilyl)oxy]methyl]-5-hexyloctahydro-pyrrolo-1H-pyrrolo[2,1-j]quinolin-7(7aH)-one

(3R,5S,7S,7aS,11aR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hexyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-decahydro-pyrrolo[2,1-j]quinoline

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