(3R,7S,10S)-10-((S)-sec-Butyl)-8,11-dioxo-14-phenylselanyl-2-oxa-6,9,12-triaza-tricyclo[13.2.2.0^3,7]nonadeca-1⁽¹⁸⁾,15⁽¹⁹⁾,16-triene-6-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (3R,7S,10S)-10-((S)-sec-Butyl)-8,11-dioxo-14-phenylselanyl-2-oxa-6,9,12-triaza-tricyclo[13.2.2.0^3,7]nonadeca-1⁽¹⁸⁾,15⁽¹⁹⁾,16-triene-6-carboxylic acid tert-butyl ester
• CAS No.: 543689-94-7
• Molecular Formula: C₃₀H₃₉N₃O₅Se
• Molecular Weight: 600.617

Synonyms:

Chemical Property of (3R,7S,10S)-10-((S)-sec-Butyl)-8,11-dioxo-14-phenylselanyl-2-oxa-6,9,12-triaza-tricyclo[13.2.2.0^3,7]nonadeca-1⁽¹⁸⁾,15⁽¹⁹⁾,16-triene-6-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,7S,10S)-10-((S)-sec-Butyl)-8,11-dioxo-14-phenylselanyl-2-oxa-6,9,12-triaza-tricyclo[13.2.2.0^3,7]nonadeca-1⁽¹⁸⁾,15⁽¹⁹⁾,16-triene-6-carboxylic acid tert-butyl ester

There total 14 articles about (3R,7S,10S)-10-((S)-sec-Butyl)-8,11-dioxo-14-phenylselanyl-2-oxa-6,9,12-triaza-tricyclo[13.2.2.0^3,7]nonadeca-1⁽¹⁸⁾,15⁽¹⁹⁾,16-triene-6-carboxylic acid tert-butyl 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:

tert-butyl (2R,3R)-2-[(tert-butyldimethylsiloxy)methyl]-3-hydroxypyrrolidine-1-carboxylate (128836-20-4) → (3R,7S,10S)-10-((S)-sec-Butyl)-8,11-dioxo-14-phenylselanyl-2-oxa-6,9,12-triaza-tricyclo[13.2.2.03,7]nonadeca-1(18),15(19),16-triene-6-carboxylic acid tert-butyl ester (543689-94-7)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 78 percent / NaH / dimethylformamide / 4 h / -30 °C

2.1: 73 percent / NaH₂PO₂ / Raney Ni / pyridine; acetic acid; H₂O / 3 h / 40 - 45 °C

3.1: 85 percent Turnov_. / Na / methanol / 0.5 h / 0 °C

4.1: 65 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

5.1: 81 percent / HCO₂NH₄ / Pd/C / methanol / 2 h / 40 °C

6.1: 91 percent / DCC; NMM; HOBt / CH₂Cl₂ / 3 h / 0 - 20 °C

7.1: 87 percent / AcOH / tetrahydrofuran; H₂O / 3 h / 45 - 50 °C

8.1: NEt₃; TFAA; DMSO / CH₂Cl₂ / 3 h / -78 °C

8.2: 65 percent / KMnO₄ / aq. phosphate buffer; 2-methyl-propan-2-ol / 1 h / 20 °C / pH 4.12

9.1: 87 percent / MeOH / Pd/C / 1 h / 20 °C

10.1: 75 percent / tetramethylfluoroformamidinium hexafluorophosphate; HOAt; DIEA / CH₂Cl₂ / 2 h / 0 °C

11.1: 60 percent / TBAF / tetrahydrofuran / 2 h / 0 - 20 °C

12.1: NEt₃ / CH₂Cl₂ / 0.5 h / -10 °C

13.1: NaBH₄ / ethanol / 0.5 h / 80 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; methanol; sodium tetrahydroborate; sodium hypophosphite; 1-hydroxy-7-aza-benzotriazole; tetrabutyl ammonium fluoride; ammonium formate; sodium; sodium hydride; benzotriazol-1-ol; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate; trifluoroacetic anhydride; palladium on activated charcoal; nickel; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; 3.1: Henry reaction / 8.1: Swern-Masamune oxidation / 10.1: Carpino method;

DOI:10.1016/S0040-4039(03)00278-8

Reference yield:

(4R,5S)-5-<(1,1-dimethylethyl)dimethylsilyl>oxymethyl-4-hydroxy-1-<(1,1-dimethylethoxy)carbonyl>-pyrrolidin-2-one (123278-55-7) → (3R,7S,10S)-10-((S)-sec-Butyl)-8,11-dioxo-14-phenylselanyl-2-oxa-6,9,12-triaza-tricyclo[13.2.2.03,7]nonadeca-1(18),15(19),16-triene-6-carboxylic acid tert-butyl ester (543689-94-7)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 88 percent / BH₃*SMe₂ / tetrahydrofuran / 5 h / Heating

2.1: 78 percent / NaH / dimethylformamide / 4 h / -30 °C

3.1: 73 percent / NaH₂PO₂ / Raney Ni / pyridine; acetic acid; H₂O / 3 h / 40 - 45 °C

4.1: 85 percent Turnov_. / Na / methanol / 0.5 h / 0 °C

5.1: 65 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

6.1: 81 percent / HCO₂NH₄ / Pd/C / methanol / 2 h / 40 °C

7.1: 91 percent / DCC; NMM; HOBt / CH₂Cl₂ / 3 h / 0 - 20 °C

8.1: 87 percent / AcOH / tetrahydrofuran; H₂O / 3 h / 45 - 50 °C

9.1: NEt₃; TFAA; DMSO / CH₂Cl₂ / 3 h / -78 °C

9.2: 65 percent / KMnO₄ / aq. phosphate buffer; 2-methyl-propan-2-ol / 1 h / 20 °C / pH 4.12

10.1: 87 percent / MeOH / Pd/C / 1 h / 20 °C

11.1: 75 percent / tetramethylfluoroformamidinium hexafluorophosphate; HOAt; DIEA / CH₂Cl₂ / 2 h / 0 °C

12.1: 60 percent / TBAF / tetrahydrofuran / 2 h / 0 - 20 °C

13.1: NEt₃ / CH₂Cl₂ / 0.5 h / -10 °C

14.1: NaBH₄ / ethanol / 0.5 h / 80 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; methanol; sodium tetrahydroborate; sodium hypophosphite; 1-hydroxy-7-aza-benzotriazole; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; ammonium formate; sodium; sodium hydride; benzotriazol-1-ol; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate; trifluoroacetic anhydride; palladium on activated charcoal; nickel; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; 4.1: Henry reaction / 9.1: Swern-Masamune oxidation / 11.1: Carpino method;

DOI:10.1016/S0040-4039(03)00278-8

Reference yield:

2-(tert-butyl-dimethyl-silanyloxymethyl)-3-(4-formyl-phenoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (540508-45-0) → (3R,7S,10S)-10-((S)-sec-Butyl)-8,11-dioxo-14-phenylselanyl-2-oxa-6,9,12-triaza-tricyclo[13.2.2.03,7]nonadeca-1(18),15(19),16-triene-6-carboxylic acid tert-butyl ester (543689-94-7)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 85 percent Turnov_. / Na / methanol / 0.5 h / 0 °C

2.1: 65 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

3.1: 81 percent / HCO₂NH₄ / Pd/C / methanol / 2 h / 40 °C

4.1: 91 percent / DCC; NMM; HOBt / CH₂Cl₂ / 3 h / 0 - 20 °C

5.1: 87 percent / AcOH / tetrahydrofuran; H₂O / 3 h / 45 - 50 °C

6.1: NEt₃; TFAA; DMSO / CH₂Cl₂ / 3 h / -78 °C

6.2: 65 percent / KMnO₄ / aq. phosphate buffer; 2-methyl-propan-2-ol / 1 h / 20 °C / pH 4.12

7.1: 87 percent / MeOH / Pd/C / 1 h / 20 °C

8.1: 75 percent / tetramethylfluoroformamidinium hexafluorophosphate; HOAt; DIEA / CH₂Cl₂ / 2 h / 0 °C

9.1: 60 percent / TBAF / tetrahydrofuran / 2 h / 0 - 20 °C

10.1: NEt₃ / CH₂Cl₂ / 0.5 h / -10 °C

11.1: NaBH₄ / ethanol / 0.5 h / 80 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; methanol; sodium tetrahydroborate; 1-hydroxy-7-aza-benzotriazole; tetrabutyl ammonium fluoride; ammonium formate; sodium; benzotriazol-1-ol; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate; trifluoroacetic anhydride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; 1.1: Henry reaction / 6.1: Swern-Masamune oxidation / 8.1: Carpino method;

DOI:10.1016/S0040-4039(03)00278-8

upstream raw materials:

diphenyl diselenide

tert-butyl (2R,3R)-2-[(tert-butyldimethylsiloxy)methyl]-3-hydroxypyrrolidine-1-carboxylate

(4R,5S)-5-<(1,1-dimethylethyl)dimethylsilyl>oxymethyl-4-hydroxy-1-<(1,1-dimethylethoxy)carbonyl>-pyrrolidin-2-one

2-(tert-butyl-dimethyl-silanyloxymethyl)-3-(4-formyl-phenoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

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