(R)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-(dimethyl-phenyl-silanyl)-3-p-tolyl-propan-1-one

Base Information

• Chemical Name: (R)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-(dimethyl-phenyl-silanyl)-3-p-tolyl-propan-1-one
• CAS No.: 153141-31-2
• Molecular Formula: C₂₈H₃₇NO₃SSi
• Molecular Weight: 495.758

Synonyms:(R)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-(dimethyl-phenyl-silanyl)-3-p-tolyl-propan-1-one

Chemical Property of (R)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-(dimethyl-phenyl-silanyl)-3-p-tolyl-propan-1-one

Chemical Property:

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Technology Process of (R)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-(dimethyl-phenyl-silanyl)-3-p-tolyl-propan-1-one

There total 1 articles about (R)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-(dimethyl-phenyl-silanyl)-3-p-tolyl-propan-1-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:

dimethyl(phenyl)silyllithium (3839-31-4) + (-)-(2E)-3-(4-methylphenyl)-1-[(3aS,6R,7aR)tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]prop-2-en-1-one (153141-24-3) → (R)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-(dimethyl-phenyl-silanyl)-3-p-tolyl-propan-1-one (153141-31-2) + (S)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-(dimethyl-phenyl-silanyl)-3-p-tolyl-propan-1-one

Guidance literature:

With 1.) CuCN; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, 0 deg C, 20 min, 2.) THF, -78 deg C, 6 h;

DOI:10.1021/jo00080a041

Reference yield: 71.0%

(R)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-(dimethyl-phenyl-silanyl)-3-p-tolyl-propan-1-one (153141-31-2) → (R)-3-(Dimethyl-phenyl-silanyl)-3-p-tolyl-propionic acid (153141-36-7)

Guidance literature:

With lithium hydroxide; tetrabutylammomium bromide; In tetrahydrofuran; water; for 96h; Ambient temperature;

DOI:10.1021/jo00080a041

Reference yield:

(R)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-(dimethyl-phenyl-silanyl)-3-p-tolyl-propan-1-one (153141-31-2) → (R)-3-(Dimethyl-phenyl-silanyl)-3-p-tolyl-propionyl chloride

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / LiOH / n-Bu₄NBr / tetrahydrofuran; H₂O / 96 h / Ambient temperature

2: (COCl)2 / CH₂Cl₂ / 0.5 h

With lithium hydroxide; oxalyl dichloride; tetrabutylammomium bromide; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/jo00080a041

upstream raw materials:

dimethyl(phenyl)silyllithium

(-)-(2E)-3-(4-methylphenyl)-1-[(3aS,6R,7aR)tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]prop-2-en-1-one

Downstream raw materials:

(R)-3-(Dimethyl-phenyl-silanyl)-3-p-tolyl-propionic acid

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