Chloro-phenylsulfanyl-acetic acid (1S,5R)-6-(toluene-4-sulfonyl)-6-aza-bicyclo[3.2.1]oct-2-en-1-yl ester

Base Information

Chemical Name:Chloro-phenylsulfanyl-acetic acid (1S,5R)-6-(toluene-4-sulfonyl)-6-aza-bicyclo[3.2.1]oct-2-en-1-yl ester
CAS No.:289710-36-7
Molecular Formula:C₂₂H₂₂ClNO₄S₂
Molecular Weight:464.006
Hs Code.:

Synonyms:Chloro-phenylsulfanyl-acetic acid (1S,5R)-6-(toluene-4-sulfonyl)-6-aza-bicyclo[3.2.1]oct-2-en-1-yl ester

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Chemical Property of Chloro-phenylsulfanyl-acetic acid (1S,5R)-6-(toluene-4-sulfonyl)-6-aza-bicyclo[3.2.1]oct-2-en-1-yl ester

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Technology Process of Chloro-phenylsulfanyl-acetic acid (1S,5R)-6-(toluene-4-sulfonyl)-6-aza-bicyclo[3.2.1]oct-2-en-1-yl ester

There total 9 articles about Chloro-phenylsulfanyl-acetic acid (1S,5R)-6-(toluene-4-sulfonyl)-6-aza-bicyclo[3.2.1]oct-2-en-1-yl 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: 81.0%

: 289710-52-7
(1S,5R)-6-(Toluene-4-sulfonyl)-6-aza-bicyclo[3.2.1]oct-2-en-1-ol

: 137469-71-7
α-chloro-α-phenylthioacetylchloride

: 289710-36-7
Chloro-phenylsulfanyl-acetic acid (1S,5R)-6-(toluene-4-sulfonyl)-6-aza-bicyclo[3.2.1]oct-2-en-1-yl ester

Guidance literature:: at 0 - 20 ℃;
DOI:10.1021/jo000260z

Reference yield:

: 261156-79-0
(E)-3-[(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-acrylonitrile

: 289710-36-7
Chloro-phenylsulfanyl-acetic acid (1S,5R)-6-(toluene-4-sulfonyl)-6-aza-bicyclo[3.2.1]oct-2-en-1-yl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 98 percent / H₂ / Pd/C / ethyl acetate / 12 h / 760.05 Torr

2: 100 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

3: 84 percent / Jones reagent / acetone / 0.5 h / 20 °C

4: 78 percent / SmI₂; MeOH / tetrahydrofuran / -78 - 20 °C

5: 91 percent / DIPEA / CH₂Cl₂ / 17 h / 0 - 20 °C

6: methanol / 20 h / 0 - 20 °C

7: 1.3 g / NaH / toluene / 3 h / Heating

8: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

9: 81 percent / 0 - 20 °C

With methanol; jones reagent; samarium diiodide; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; acetone; toluene; 1: Catalytic hydrogenation / 2: desilylation / 3: Oxidation / 4: Cyclization / 5: Condensation / 6: Condensation / 7: Reduction / 8: deprotection / 9: Acylation;
DOI:10.1021/jo000260z

Reference yield:

: 261156-80-3
3-[(R)-4-Oxo-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionitrile

: 289710-36-7
Chloro-phenylsulfanyl-acetic acid (1S,5R)-6-(toluene-4-sulfonyl)-6-aza-bicyclo[3.2.1]oct-2-en-1-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 78 percent / SmI₂; MeOH / tetrahydrofuran / -78 - 20 °C

2: 91 percent / DIPEA / CH₂Cl₂ / 17 h / 0 - 20 °C

3: methanol / 20 h / 0 - 20 °C

4: 1.3 g / NaH / toluene / 3 h / Heating

5: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

6: 81 percent / 0 - 20 °C

With methanol; samarium diiodide; tetrabutyl ammonium fluoride; sodium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; toluene; 1: Cyclization / 2: Condensation / 3: Condensation / 4: Reduction / 5: deprotection / 6: Acylation;
DOI:10.1021/jo000260z