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-ol

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-ol
• CAS No.: 780820-87-3
• Molecular Formula: C₃₅H₅₃NO₄SSi
• Molecular Weight: 611.962

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-ol

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-ol

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-ol

There total 9 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-ol 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) + 1,2-Epoxyoctane (2984-50-1) → 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-ol (780820-87-3)

Guidance literature:

3-(tert-butyl-diphenyl-silanyloxymethyl)-octahydro-4-thia-3a-aza-cyclopenta[c]indene 4,4-dioxide; With tert.-butyl lithium; In tetrahydrofuran; at -78 ℃; for 0.25h;

1,2-Epoxyoctane; With boron trifluoride diethyl etherate; In tetrahydrofuran; at -78 - 0 ℃; for 3h;

DOI:10.1002/anie.200460178

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-ol (780820-87-3)

Guidance literature:

Multi-step reaction with 7 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

With 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; [bis(acetoxy)iodo]benzene; tert.-butyl lithium; potassium hexamethylsilazane; 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-ol (780820-87-3)

Guidance literature:

Multi-step reaction with 3 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

With 1H-imidazole; tert.-butyl lithium; potassium hexamethylsilazane; In tetrahydrofuran; 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:

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

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

(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,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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