(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-[(R)-2-(4-phenyl-butyl)-2,3-dihydro-benzofuran-4-yl]-propenone

Base Information

• Chemical Name: (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-[(R)-2-(4-phenyl-butyl)-2,3-dihydro-benzofuran-4-yl]-propenone
• CAS No.: 532400-23-0
• Molecular Formula: C₃₁H₃₇NO₄S
• Molecular Weight: 519.705

Synonyms:(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-[(R)-2-(4-phenyl-butyl)-2,3-dihydro-benzofuran-4-yl]-propenone

Chemical Property of (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-[(R)-2-(4-phenyl-butyl)-2,3-dihydro-benzofuran-4-yl]-propenone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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-[(R)-2-(4-phenyl-butyl)-2,3-dihydro-benzofuran-4-yl]-propenone

There total 13 articles about (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-[(R)-2-(4-phenyl-butyl)-2,3-dihydro-benzofuran-4-yl]-propenone 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:

2-allyl-3-hydroxybenzoic acid ethyl ester (53596-59-1) → (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-[(R)-2-(4-phenyl-butyl)-2,3-dihydro-benzofuran-4-yl]-propenone (532400-23-0)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 96 percent / i-Pr₂NEt / CH₂Cl₂ / 20 °C

2.1: 74 percent / OsO₄; aq. NaIO₄ / ethyl acetate / 20 °C

3.1: (-)-B-methoxydisopinocampheylborane / diethyl ether

4.1: BH₃ / tetrahydrofuran

4.2: 75 percent / aq. H₂O₂; NaOH / tetrahydrofuran

5.1: 90 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂

6.1: 86 percent / n-BuLi / tetrahydrofuran

7.1: 99 percent / H₂ / Pd/C / ethyl acetate

8.1: 99 percent / DIBAL-H / toluene / -78 °C

9.1: 98 percent / tetrahydrofuran / Heating

10.1: 100 percent / HCl / ethanol / 20 °C

11.1: 95 percent / Ph₃P; diethyl azodicarboxylate / tetrahydrofuran / 0 - 25 °C

12.1: 96 percent / aq. NaOH / methanol / Heating

13.1: SOCl₂ / CH₂Cl₂ / Heating

14.1: NaH / toluene / 0 - 25 °C

With hydrogenchloride; sodium hydroxide; sodium periodate; osmium(VIII) oxide; n-butyllithium; thionyl chloride; oxalyl dichloride; borane; hydrogen; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; (-)-B-methoxydiisopinocampheylborane; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; ethyl acetate; toluene; 5.1: Swern oxidation / 6.1: Wittig reaction / 9.1: Wittig reaction / 11.1: Mitsunobu reaction;

DOI:10.1016/j.bmcl.2005.01.015

Reference yield:

benzyltriphenylphosphonium bromide (1449-46-3) → (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-[(R)-2-(4-phenyl-butyl)-2,3-dihydro-benzofuran-4-yl]-propenone (532400-23-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 86 percent / n-BuLi / tetrahydrofuran

2: 99 percent / H₂ / Pd/C / ethyl acetate

3: 99 percent / DIBAL-H / toluene / -78 °C

4: 98 percent / tetrahydrofuran / Heating

5: 100 percent / HCl / ethanol / 20 °C

6: 95 percent / Ph₃P; diethyl azodicarboxylate / tetrahydrofuran / 0 - 25 °C

7: 96 percent / aq. NaOH / methanol / Heating

8: SOCl₂ / CH₂Cl₂ / Heating

9: NaH / toluene / 0 - 25 °C

With hydrogenchloride; sodium hydroxide; n-butyllithium; thionyl chloride; hydrogen; sodium hydride; diisobutylaluminium hydride; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; toluene; 1: Wittig reaction / 4: Wittig reaction / 6: Mitsunobu reaction;

DOI:10.1016/j.bmcl.2005.01.015

Reference yield:

ethyl 3-(Methoxymethoxy)-2-(2-oxoethyl)benzoate (532399-60-3) → (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-[(R)-2-(4-phenyl-butyl)-2,3-dihydro-benzofuran-4-yl]-propenone (532400-23-0)

Guidance literature:

Multi-step reaction with 12 steps

1.1: (-)-B-methoxydisopinocampheylborane / diethyl ether

2.1: BH₃ / tetrahydrofuran

2.2: 75 percent / aq. H₂O₂; NaOH / tetrahydrofuran

3.1: 90 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂

4.1: 86 percent / n-BuLi / tetrahydrofuran

5.1: 99 percent / H₂ / Pd/C / ethyl acetate

6.1: 99 percent / DIBAL-H / toluene / -78 °C

7.1: 98 percent / tetrahydrofuran / Heating

8.1: 100 percent / HCl / ethanol / 20 °C

9.1: 95 percent / Ph₃P; diethyl azodicarboxylate / tetrahydrofuran / 0 - 25 °C

10.1: 96 percent / aq. NaOH / methanol / Heating

11.1: SOCl₂ / CH₂Cl₂ / Heating

12.1: NaH / toluene / 0 - 25 °C

With hydrogenchloride; sodium hydroxide; n-butyllithium; thionyl chloride; oxalyl dichloride; borane; hydrogen; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; (-)-B-methoxydiisopinocampheylborane; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; ethyl acetate; toluene; 3.1: Swern oxidation / 4.1: Wittig reaction / 7.1: Wittig reaction / 9.1: Mitsunobu reaction;

DOI:10.1016/j.bmcl.2005.01.015

upstream raw materials:

(2R)-bornane-10,2-sultam

2-allyl-3-hydroxybenzoic acid ethyl ester

benzyltriphenylphosphonium bromide

ethyl 3-(Methoxymethoxy)-2-(2-oxoethyl)benzoate

Downstream raw materials:

((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-{(1R,2R)-2-[(R)-2-(4-phenyl-butyl)-2,3-dihydro-benzofuran-4-yl]-cyclopropyl}-methanone

1-Ethyl-3-{(1R,2R)-2-[(R)-2-(4-phenyl-butyl)-2,3-dihydro-benzofuran-4-yl]-cyclopropylmethyl}-urea

{(1R,2R)-2-[(R)-2-(4-Phenyl-butyl)-2,3-dihydro-benzofuran-4-yl]-cyclopropyl}-methanol

C-{(1R,2R)-2-[(R)-2-(4-Phenyl-butyl)-2,3-dihydro-benzofuran-4-yl]-cyclopropyl}-methylamine

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