(3R,6R,7R,10R,11R)-10-(tert-Butyl-dimethyl-silanyloxy)-3,11-diethyl-7-methyl-2-oxo-azacyclotetradecane-6-carboselenoic acid Se-phenyl ester

Base Information

• Chemical Name: (3R,6R,7R,10R,11R)-10-(tert-Butyl-dimethyl-silanyloxy)-3,11-diethyl-7-methyl-2-oxo-azacyclotetradecane-6-carboselenoic acid Se-phenyl ester
• CAS No.: 194654-06-3
• Molecular Formula: C₃₁H₅₃NO₃SeSi
• Molecular Weight: 594.812

Synonyms:

Chemical Property of (3R,6R,7R,10R,11R)-10-(tert-Butyl-dimethyl-silanyloxy)-3,11-diethyl-7-methyl-2-oxo-azacyclotetradecane-6-carboselenoic acid Se-phenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,6R,7R,10R,11R)-10-(tert-Butyl-dimethyl-silanyloxy)-3,11-diethyl-7-methyl-2-oxo-azacyclotetradecane-6-carboselenoic acid Se-phenyl ester

There total 21 articles about (3R,6R,7R,10R,11R)-10-(tert-Butyl-dimethyl-silanyloxy)-3,11-diethyl-7-methyl-2-oxo-azacyclotetradecane-6-carboselenoic acid Se-phenyl 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:

(R)-5-azido-2-ethylpentanal (194653-99-1) → (3R,6R,7R,10R,11R)-10-(tert-Butyl-dimethyl-silanyloxy)-3,11-diethyl-7-methyl-2-oxo-azacyclotetradecane-6-carboselenoic acid Se-phenyl ester (194654-06-3)

Guidance literature:

Multi-step reaction with 15 steps

1: 85 percent / NaH / tetrahydrofuran / Ambient temperature

2: 95 percent / DIBAL-H / tetrahydrofuran / -78 °C

3: 70 percent / Ti(O-i-C₃H₇)4, (-)-DET, MS 4A / CH₂Cl₂ / 0 °C

4: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) -78 deg C

5: KN(SiMe₃)2 / tetrahydrofuran

6: 75 percent / <(dba)3Pd₂*CHCl₃>, 4-ethyl-2,6,7-trioxa-1-phosphabicyclo<2.2.2>octane / tetrahydrofuran / 12 h / Ambient temperature

7: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

8: aq. HCO₂NH₄ / 1.5percent Pd/C / 3000240 Torr / Ambient temperature

9: PyBroP, (i-Pr)2NEt, DMAP / toluene / 83 °C

10: 1.) aq. LiOH / 1.) r.t., 4 kbar, 2.) DMSO, 120 deg C

11: TBAF / tetrahydrofuran / 0 - 40 °C

12: H₂ / 10percent Pd/C / ethanol / Ambient temperature

13: 2,6-lutidine / CH₂Cl₂ / 0 °C

14: aq. LiOH, KCN / methanol; tetrahydrofuran / Ambient temperature

15: 1.) PhOP(O)Cl₂, Et₃N, 2.) Et₃N / 1.) THF, 0 deg C, 2.) 0 deg C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; dmap; potassium cyanide; lithium hydroxide; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; ammonium formate; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; O-phenyl phosphorodichloridate; (-)-diethyl tartrate; triethylamine; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; palladium on activated charcoal; ethriol phosphite; In tetrahydrofuran; methanol; ethanol; dichloromethane; toluene;

DOI:10.1002/anie.199714861

Reference yield:

(R)-2-Ethyl-pent-4-enoic acid benzyl ester (194653-95-7) → (3R,6R,7R,10R,11R)-10-(tert-Butyl-dimethyl-silanyloxy)-3,11-diethyl-7-methyl-2-oxo-azacyclotetradecane-6-carboselenoic acid Se-phenyl ester (194654-06-3)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C

2: 87 percent / NaTeH, piperidine, HOAc / ethanol

3: 75 percent / <(dba)3Pd₂*CHCl₃>, 4-ethyl-2,6,7-trioxa-1-phosphabicyclo<2.2.2>octane / tetrahydrofuran / 12 h / Ambient temperature

4: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

5: aq. HCO₂NH₄ / 1.5percent Pd/C / 3000240 Torr / Ambient temperature

6: PyBroP, (i-Pr)2NEt, DMAP / toluene / 83 °C

7: 1.) aq. LiOH / 1.) r.t., 4 kbar, 2.) DMSO, 120 deg C

8: TBAF / tetrahydrofuran / 0 - 40 °C

9: H₂ / 10percent Pd/C / ethanol / Ambient temperature

10: 2,6-lutidine / CH₂Cl₂ / 0 °C

11: aq. LiOH, KCN / methanol; tetrahydrofuran / Ambient temperature

12: 1.) PhOP(O)Cl₂, Et₃N, 2.) Et₃N / 1.) THF, 0 deg C, 2.) 0 deg C

With piperidine; 2,6-dimethylpyridine; dmap; potassium cyanide; lithium hydroxide; sodium hydrogen telluride; tetrabutyl ammonium fluoride; hydrogen; ammonium formate; ozone; acetic acid; O-phenyl phosphorodichloridate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; palladium on activated charcoal; ethriol phosphite; In tetrahydrofuran; methanol; ethanol; dichloromethane; toluene;

DOI:10.1002/anie.199714861

Reference yield:

(E)-(R)-7-Azido-4-ethyl-hept-2-en-1-ol (194654-13-2) → (3R,6R,7R,10R,11R)-10-(tert-Butyl-dimethyl-silanyloxy)-3,11-diethyl-7-methyl-2-oxo-azacyclotetradecane-6-carboselenoic acid Se-phenyl ester (194654-06-3)

Guidance literature:

Multi-step reaction with 13 steps

1: 70 percent / Ti(O-i-C₃H₇)4, (-)-DET, MS 4A / CH₂Cl₂ / 0 °C

2: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) -78 deg C

3: KN(SiMe₃)2 / tetrahydrofuran

4: 75 percent / <(dba)3Pd₂*CHCl₃>, 4-ethyl-2,6,7-trioxa-1-phosphabicyclo<2.2.2>octane / tetrahydrofuran / 12 h / Ambient temperature

5: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

6: aq. HCO₂NH₄ / 1.5percent Pd/C / 3000240 Torr / Ambient temperature

7: PyBroP, (i-Pr)2NEt, DMAP / toluene / 83 °C

8: 1.) aq. LiOH / 1.) r.t., 4 kbar, 2.) DMSO, 120 deg C

9: TBAF / tetrahydrofuran / 0 - 40 °C

10: H₂ / 10percent Pd/C / ethanol / Ambient temperature

11: 2,6-lutidine / CH₂Cl₂ / 0 °C

12: aq. LiOH, KCN / methanol; tetrahydrofuran / Ambient temperature

13: 1.) PhOP(O)Cl₂, Et₃N, 2.) Et₃N / 1.) THF, 0 deg C, 2.) 0 deg C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; dmap; potassium cyanide; lithium hydroxide; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; ammonium formate; potassium hexamethylsilazane; dimethyl sulfoxide; O-phenyl phosphorodichloridate; (-)-diethyl tartrate; triethylamine; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; palladium on activated charcoal; ethriol phosphite; In tetrahydrofuran; methanol; ethanol; dichloromethane; toluene;

DOI:10.1002/anie.199714861

upstream raw materials:

Benzeneselenol

(R)-5-azido-2-ethyl-1-pentanol

(R)-5-azido-2-ethylpentanal

(E)-(R)-7-Azido-4-ethyl-hept-2-en-1-ol

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