(Z)-(1S,9S,10S,14S)-11-(tert-Butyl-dimethyl-silanyl)-1-(tert-butyl-dimethyl-silanyloxy)-9-phenylselanyl-13-oxa-11-aza-tricyclo[7.6.1.0^10,14]hexadec-4-ene-2,6-diyne-12,16-dione

Base Information

• Chemical Name: (Z)-(1S,9S,10S,14S)-11-(tert-Butyl-dimethyl-silanyl)-1-(tert-butyl-dimethyl-silanyloxy)-9-phenylselanyl-13-oxa-11-aza-tricyclo[7.6.1.0^10,14]hexadec-4-ene-2,6-diyne-12,16-dione
• CAS No.: 140150-21-6
• Molecular Formula: C₃₂H₄₃NO₄SeSi₂
• Molecular Weight: 640.829

Synonyms:(Z)-(1S,9S,10S,14S)-11-(tert-Butyl-dimethyl-silanyl)-1-(tert-butyl-dimethyl-silanyloxy)-9-phenylselanyl-13-oxa-11-aza-tricyclo[7.6.1.0^10,14]hexadec-4-ene-2,6-diyne-12,16-dione

Chemical Property of (Z)-(1S,9S,10S,14S)-11-(tert-Butyl-dimethyl-silanyl)-1-(tert-butyl-dimethyl-silanyloxy)-9-phenylselanyl-13-oxa-11-aza-tricyclo[7.6.1.0^10,14]hexadec-4-ene-2,6-diyne-12,16-dione

Chemical Property:

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Technology Process of (Z)-(1S,9S,10S,14S)-11-(tert-Butyl-dimethyl-silanyl)-1-(tert-butyl-dimethyl-silanyloxy)-9-phenylselanyl-13-oxa-11-aza-tricyclo[7.6.1.0^10,14]hexadec-4-ene-2,6-diyne-12,16-dione

There total 10 articles about (Z)-(1S,9S,10S,14S)-11-(tert-Butyl-dimethyl-silanyl)-1-(tert-butyl-dimethyl-silanyloxy)-9-phenylselanyl-13-oxa-11-aza-tricyclo[7.6.1.0^10,14]hexadec-4-ene-2,6-diyne-12,16-dione 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:

t-butyldimethylsiyl triflate (69739-34-0) → (Z)-(1S,9S,10S,14S)-11-(tert-Butyl-dimethyl-silanyl)-1-(tert-butyl-dimethyl-silanyloxy)-9-phenylselanyl-13-oxa-11-aza-tricyclo[7.6.1.010,14]hexadec-4-ene-2,6-diyne-12,16-dione (140150-21-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) 0.5 M potassium bis(trimethylsilyl)amide / 1.) THF, toluene, -78 deg C, 5 min, 2.) THF, toluene, -78 deg C, 20 min

2: 1.) phenylselenyl chloride, 2.) pyridine, 30percent aq. H₂O₂ / 1.) dichloromethane, -78 deg C, 15 min, 2.) dichloromethane, RT, 1 h

3: 52 percent / DBU / tetrahydrofuran / 42 h / 20 °C

4: 76 percent / pyridine, 30percent aq. H₂O₂ / CH₂Cl₂ / -20 - 20 °C

5: 89 percent / trifluoroacetic acid / CH₂Cl₂ / 4 h / 25 °C

6: 95 percent / triethylamine / CH₂Cl₂ / 0.17 h / 25 °C

7: 1.) potassium bis(trimethylsilyl)amide, 2.) N-(phenylseleneno)phthalimide / 1.) THF, -78 deg C, 15 min, 2.) THF, -78 deg C, 1 h

With pyridine; Phenylselenyl chloride; N-phenylselanylphthalimide; dihydrogen peroxide; potassium hexamethylsilazane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00033a032

Reference yield:

13-keto-5-<(tert-butyldimethylsilyl)oxy>bicyclo<7.3.1>tridec-8-ene-6,10-diyne (116669-92-2,125409-41-8,140224-07-3,150737-51-2) → (Z)-(1S,9S,10S,14S)-11-(tert-Butyl-dimethyl-silanyl)-1-(tert-butyl-dimethyl-silanyloxy)-9-phenylselanyl-13-oxa-11-aza-tricyclo[7.6.1.010,14]hexadec-4-ene-2,6-diyne-12,16-dione (140150-21-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) 0.5 M potassium bis(trimethylsilyl)amide / 1.) THF, toluene, -78 deg C, 5 min, 2.) THF, toluene, -78 deg C, 20 min

2: 1.) phenylselenyl chloride, 2.) pyridine, 30percent aq. H₂O₂ / 1.) dichloromethane, -78 deg C, 15 min, 2.) dichloromethane, RT, 1 h

3: 52 percent / DBU / tetrahydrofuran / 42 h / 20 °C

4: 76 percent / pyridine, 30percent aq. H₂O₂ / CH₂Cl₂ / -20 - 20 °C

5: 89 percent / trifluoroacetic acid / CH₂Cl₂ / 4 h / 25 °C

6: 95 percent / triethylamine / CH₂Cl₂ / 0.17 h / 25 °C

7: 1.) potassium bis(trimethylsilyl)amide, 2.) N-(phenylseleneno)phthalimide / 1.) THF, -78 deg C, 15 min, 2.) THF, -78 deg C, 1 h

With pyridine; Phenylselenyl chloride; N-phenylselanylphthalimide; dihydrogen peroxide; potassium hexamethylsilazane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00033a032

Reference yield:

5,13-bis<(tert-butyldimethylsilyl)oxy>bicyclo<7.3.1>trideca-8,13-diene-6,10-diyne (124842-62-2) → (Z)-(1S,9S,10S,14S)-11-(tert-Butyl-dimethyl-silanyl)-1-(tert-butyl-dimethyl-silanyloxy)-9-phenylselanyl-13-oxa-11-aza-tricyclo[7.6.1.010,14]hexadec-4-ene-2,6-diyne-12,16-dione (140150-21-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) phenylselenyl chloride, 2.) pyridine, 30percent aq. H₂O₂ / 1.) dichloromethane, -78 deg C, 15 min, 2.) dichloromethane, RT, 1 h

2: 52 percent / DBU / tetrahydrofuran / 42 h / 20 °C

3: 76 percent / pyridine, 30percent aq. H₂O₂ / CH₂Cl₂ / -20 - 20 °C

4: 89 percent / trifluoroacetic acid / CH₂Cl₂ / 4 h / 25 °C

5: 95 percent / triethylamine / CH₂Cl₂ / 0.17 h / 25 °C

6: 1.) potassium bis(trimethylsilyl)amide, 2.) N-(phenylseleneno)phthalimide / 1.) THF, -78 deg C, 15 min, 2.) THF, -78 deg C, 1 h

With pyridine; Phenylselenyl chloride; N-phenylselanylphthalimide; dihydrogen peroxide; potassium hexamethylsilazane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00033a032

upstream raw materials:

C₂₆H₃₉NO₄Si₂

t-butyldimethylsiyl triflate

13-keto-5-<(tert-butyldimethylsilyl)oxy>bicyclo<7.3.1>tridec-8-ene-6,10-diyne

13-keto-5-<(tert-butyldimethylsilyl)oxy>bicyclo<7.3.1>trideca-1,8-diene-6,10-diyne

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