ethyl (3R,4R,5S)-5-(1,3-dioxoisoindolin-2-yl)-3-(pentan-3-yloxy)-4-{N-[2-(trimethylsilyl)ethylsulfonyl]acetamido}cyclohex-1-enecarboxylate

Base Information

• Chemical Name: ethyl (3R,4R,5S)-5-(1,3-dioxoisoindolin-2-yl)-3-(pentan-3-yloxy)-4-{N-[2-(trimethylsilyl)ethylsulfonyl]acetamido}cyclohex-1-enecarboxylate
• CAS No.: 1041262-67-2
• Molecular Formula: C₂₉H₄₂N₂O₈SSi
• Molecular Weight: 606.813
• Mol file: 1041262-67-2.mol

Synonyms:ethyl (3R,4R,5S)-5-(1,3-dioxoisoindolin-2-yl)-3-(pentan-3-yloxy)-4-{N-[2-(trimethylsilyl)ethylsulfonyl]acetamido}cyclohex-1-enecarboxylate

Chemical Property of ethyl (3R,4R,5S)-5-(1,3-dioxoisoindolin-2-yl)-3-(pentan-3-yloxy)-4-{N-[2-(trimethylsilyl)ethylsulfonyl]acetamido}cyclohex-1-enecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (3R,4R,5S)-5-(1,3-dioxoisoindolin-2-yl)-3-(pentan-3-yloxy)-4-{N-[2-(trimethylsilyl)ethylsulfonyl]acetamido}cyclohex-1-enecarboxylate

There total 11 articles about ethyl (3R,4R,5S)-5-(1,3-dioxoisoindolin-2-yl)-3-(pentan-3-yloxy)-4-{N-[2-(trimethylsilyl)ethylsulfonyl]acetamido}cyclohex-1-enecarboxylate 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: 84.0%

ethyl (3R,4R,5S)-5-(1,3-dioxoisoindolin-2-yl)-3-(pentan-3-yloxy)-4-[2-(trimethylsilyl)ethylsulfonamido]cyclohex-1-enecarboxylate (1041262-66-1) + acetic anhydride (108-24-7) → ethyl (3R,4R,5S)-5-(1,3-dioxoisoindolin-2-yl)-3-(pentan-3-yloxy)-4-{N-[2-(trimethylsilyl)ethylsulfonyl]acetamido}cyclohex-1-enecarboxylate (1041262-67-2)

Guidance literature:

With pyridine; dmap; at 150 ℃; for 1h; microwave irradiation;

DOI:10.1002/anie.200800282

Reference yield:

6-oxabicyclo<3.2.1>-oct-3-en-7-one (4720-83-6) → ethyl (3R,4R,5S)-5-(1,3-dioxoisoindolin-2-yl)-3-(pentan-3-yloxy)-4-{N-[2-(trimethylsilyl)ethylsulfonyl]acetamido}cyclohex-1-enecarboxylate (1041262-67-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: bis(η3-allyl-μ-chloropalladium(II)); (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane / tetrahydrofuran / 0.33 h / 40 °C / Inert atmosphere

1.2: 8 h / 40 °C / Inert atmosphere

1.3: 10 h / Inert atmosphere; Reflux

2.1: potassium hexamethylsilazane / tetrahydrofuran / 6 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / toluene / 2 h / 0 °C / Inert atmosphere

3.2: 5 h / 60 °C / Inert atmosphere

3.3: 20 °C / Inert atmosphere; Molecular sieve

4.1: boron trifluoride diethyl etherate / 75 °C / Inert atmosphere

5.1: pyridine; dmap / 1 h / 150 °C / Inert atmosphere; Microwave irradiation

With pyridine; dmap; bis(η3-allyl-μ-chloropalladium(II)); boron trifluoride diethyl etherate; potassium hexamethylsilazane; sodium hydrogencarbonate; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; toluene;

DOI:10.1002/chem.201003454

Reference yield:

ethyl (1S,5S)-5-(1,3-dioxoisoindolin-2-yl)cyclohex-3-enecarboxylate (1041262-62-7) → ethyl (3R,4R,5S)-5-(1,3-dioxoisoindolin-2-yl)-3-(pentan-3-yloxy)-4-{N-[2-(trimethylsilyl)ethylsulfonyl]acetamido}cyclohex-1-enecarboxylate (1041262-67-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium hexamethylsilazane / tetrahydrofuran / 6 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / toluene / 2 h / 0 °C / Inert atmosphere

2.2: 5 h / 60 °C / Inert atmosphere

2.3: 20 °C / Inert atmosphere; Molecular sieve

3.1: boron trifluoride diethyl etherate / 75 °C / Inert atmosphere

4.1: pyridine; dmap / 1 h / 150 °C / Inert atmosphere; Microwave irradiation

With pyridine; dmap; boron trifluoride diethyl etherate; potassium hexamethylsilazane; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; toluene;

DOI:10.1002/chem.201003454

upstream raw materials:

ethyl (3R,4R,5S)-5-(1,3-dioxoisoindolin-2-yl)-3-(pentan-3-yloxy)-4-[2-(trimethylsilyl)ethylsulfonamido]cyclohex-1-enecarboxylate

acetic anhydride

(3R,4R,5S)-ethyl 5-(1,3-dioxoisoindolin-2-yl)-3-hydroxy-4-(2-(trimethylsilyl)ethylsulfonamido)cyclohex-1-enecarboxylate

ethyl (1S,5S)-5-(1,3-dioxoisoindolin-2-yl)cyclohex-3-enecarboxylate

Downstream raw materials:

(3R,4R,5S)-4-acetamido-5-(1,3-dioxoisoindol-2-yl)-3-(pentyl-3-yloxy)cyclohexyl-ethyl-1-ene-1-carboxylate

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