ethyl (3R,4R,5S)-5-((tert-butoxycarbonyl)amino)-3-hydroxy-4-(4-methylphenylsulfonamido)cyclohex-1-ene carboxylate

Base Information

• Chemical Name: ethyl (3R,4R,5S)-5-((tert-butoxycarbonyl)amino)-3-hydroxy-4-(4-methylphenylsulfonamido)cyclohex-1-ene carboxylate
• CAS No.: 1196491-13-0
• Molecular Formula: C₂₁H₃₀N₂O₇S
• Molecular Weight: 454.544

Synonyms:ethyl (3R,4R,5S)-5-((tert-butoxycarbonyl)amino)-3-hydroxy-4-(4-methylphenylsulfonamido)cyclohex-1-ene carboxylate

Chemical Property of ethyl (3R,4R,5S)-5-((tert-butoxycarbonyl)amino)-3-hydroxy-4-(4-methylphenylsulfonamido)cyclohex-1-ene carboxylate

Chemical Property:

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Technology Process of ethyl (3R,4R,5S)-5-((tert-butoxycarbonyl)amino)-3-hydroxy-4-(4-methylphenylsulfonamido)cyclohex-1-ene carboxylate

There total 18 articles about ethyl (3R,4R,5S)-5-((tert-butoxycarbonyl)amino)-3-hydroxy-4-(4-methylphenylsulfonamido)cyclohex-1-ene carboxylate 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: 76.0%

ethyl (3aR,6S,7R,7aS)-6-[(tert-butoxycarbonyl)amino]-2,2-dimethyl-7-{[(4-methylphenyl)sulfonyl]amino}-3a,6,7,7a-tetrahydro-1,3-benzodioxole-4-carboxylate (1196491-05-0) → ethyl (3R,4R,5S)-5-((tert-butoxycarbonyl)amino)-3-hydroxy-4-(4-methylphenylsulfonamido)cyclohex-1-ene carboxylate (1196491-13-0)

Guidance literature:

ethyl (3aR,6S,7R,7aS)-6-[(tert-butoxycarbonyl)amino]-2,2-dimethyl-7-{[(4-methylphenyl)sulfonyl]amino}-3a,6,7,7a-tetrahydro-1,3-benzodioxole-4-carboxylate; With Rh/Al₂O₃; hydrogen; In ethanol; at 20 ℃; for 144h; under 2844.39 Torr; Inert atmosphere;

With sodium ethanolate; In ethanol; at 20 ℃; Inert atmosphere;

DOI:10.1021/jo2018872

Reference yield:

(+)-ethyl (5S,6R)-5,6-dihydroxycyclohexa-1,3-dienecarboxylate (1173701-22-8) → ethyl (3R,4R,5S)-5-((tert-butoxycarbonyl)amino)-3-hydroxy-4-(4-methylphenylsulfonamido)cyclohex-1-ene carboxylate (1196491-13-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: toluene-4-sulfonic acid / acetone / 20 °C / Inert atmosphere

2.1: copper acetylacetonate / acetonitrile / 5 h / 0 °C / Inert atmosphere

3.1: sodium azide; ammonium chloride / N,N-dimethyl-formamide / 3 h / 0 °C / Inert atmosphere

4.1: triphenylphosphine / tetrahydrofuran; water / 12 h

5.1: triethylamine / dichloromethane / 12 h / 0 °C / Inert atmosphere

6.1: Rh/Al₂O₃; hydrogen / ethanol / 144 h / 20 °C / 2844.39 Torr / Inert atmosphere

6.2: 20 °C / Inert atmosphere

With copper acetylacetonate; sodium azide; Rh/Al₂O₃; hydrogen; ammonium chloride; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; 4.1: Staudinger reaction;

DOI:10.1021/jo2018872

Reference yield:

C16H21BrN2O4S (1349901-42-3) → ethyl (3R,4R,5S)-5-((tert-butoxycarbonyl)amino)-3-hydroxy-4-(4-methylphenylsulfonamido)cyclohex-1-ene carboxylate (1196491-13-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine / dichloromethane / 12 h / 0 °C / Inert atmosphere

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / ethanol; toluene / 1 h / 60 °C / Inert atmosphere

2.2: 6 h / Reflux; Inert atmosphere

3.1: Rh/Al₂O₃; hydrogen / ethanol / 144 h / 20 °C / 2844.39 Torr / Inert atmosphere

3.2: 20 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; Rh/Al₂O₃; hydrogen; triethylamine; In ethanol; dichloromethane; toluene;

DOI:10.1021/jo2018872

upstream raw materials:

(+)-ethyl (5S,6R)-5,6-dihydroxycyclohexa-1,3-dienecarboxylate

(+)-ethyl (3aR,7aS)-2,2-dimethyl-3a,7a-dihydrobenzo[d][1,3]dioxole-4-carboxylate

C₁₆H₁₈INO₄S

N-[(3aS,4R,5S,7aS)-5-azido-7-bromo-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-4-yl]-4-methylbenzenesulfonamide

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