(S)-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)-butan-1-one

Base Information

• Chemical Name: (S)-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)-butan-1-one
• CAS No.: 109120-45-8
• Molecular Formula: C₂₂H₃₃NO₃SSi
• Molecular Weight: 419.66
• Mol file: 109120-45-8.mol

Synonyms:(S)-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)-butan-1-one

Chemical Property of (S)-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)-butan-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-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)-butan-1-one

There total 4 articles about (S)-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)-butan-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: 61.0%

methyllithium (917-54-4) + (E)-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)-propenone (109053-72-7) → (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)-butan-1-one (109120-45-8) + (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)-butan-1-one

Guidance literature:

With copper(l) iodide; tributylphosphine; ethylaluminum dichloride; In diethyl ether; at -78 ℃; for 2h; Yields of byproduct given;

DOI:10.1002/hlca.19860690703

Reference yield:

phenyldimethylsilyl chloride (768-33-2) → (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)-butan-1-one (109120-45-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1., BuLi, 2., BuLi / -78 deg C

2: 1., oxalyl chloride 2., NaH

3: CuI, Bu₃P, EtAlCl₂ / diethyl ether / 2 h / -78 °C

With copper(l) iodide; n-butyllithium; oxalyl dichloride; tributylphosphine; ethylaluminum dichloride; sodium hydride; In diethyl ether;

DOI:10.1002/hlca.19860690703

Reference yield:

(E)-3-[dimethyl(phenyl)silyl]propenoic acid (109053-88-5) → (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)-butan-1-one (109120-45-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1., oxalyl chloride 2., NaH

2: CuI, Bu₃P, EtAlCl₂ / diethyl ether / 2 h / -78 °C

With copper(l) iodide; oxalyl dichloride; tributylphosphine; ethylaluminum dichloride; sodium hydride; In diethyl ether;

DOI:10.1002/hlca.19860690703

upstream raw materials:

methyllithium

(E)-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)-propenone

dimethyl(phenyl)silyllithium

(1S)-N-crotyl-2,10-camphorsultam

Downstream raw materials:

(3S,4R)-4-benzoyl-3-<1(S)-(dimethylphenylsilyl)ethyl>-1-(p-methoxyphenyl)azetidin-2-one

(3R,4R)-4-Benzoyl-3-[(S)-1-(fluoro-dimethyl-silanyl)-ethyl]-1-(4-methoxy-phenyl)-azetidin-2-one

β-(dimethylphenylsilyl)butanoyl chloride

(S)-3-(dimethyl(phenyl)silyl)butanoic acid