(1S,3R,5RS,7S,8R,9S,11S)-7-(tert-Butyldimethylsilyloxy)-5-phenylseleno-2,4,10-trioxatetracyclo<6.3.1.0^3,7.0^9,11>dodecane

Base Information

• Chemical Name: (1S,3R,5RS,7S,8R,9S,11S)-7-(tert-Butyldimethylsilyloxy)-5-phenylseleno-2,4,10-trioxatetracyclo<6.3.1.0^3,7.0^9,11>dodecane
• CAS No.: 137956-43-5
• Molecular Formula: C₂₁H₃₀O₄SeSi
• Molecular Weight: 453.512
• Mol file: 137956-43-5.mol

Synonyms:

Chemical Property of (1S,3R,5RS,7S,8R,9S,11S)-7-(tert-Butyldimethylsilyloxy)-5-phenylseleno-2,4,10-trioxatetracyclo<6.3.1.0^3,7.0^9,11>dodecane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3R,5RS,7S,8R,9S,11S)-7-(tert-Butyldimethylsilyloxy)-5-phenylseleno-2,4,10-trioxatetracyclo<6.3.1.0^3,7.0^9,11>dodecane

There total 16 articles about (1S,3R,5RS,7S,8R,9S,11S)-7-(tert-Butyldimethylsilyloxy)-5-phenylseleno-2,4,10-trioxatetracyclo<6.3.1.0^3,7.0^9,11>dodecane 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: 44.0%

Benzeneselenol (645-96-5) + (1S,3R,5RS,7S,8R,9S,11S)-7-(tert-Butyldimethylsilyloxy)-5-methoxy-2,4,10-trioxatetracyclo<6.3.1.03,7.09,11>dodecane (130486-19-0,138052-00-3,138052-09-2) → (1S,3R,5RS,7S,8R,9S,11S)-7-(tert-Butyldimethylsilyloxy)-5-phenylseleno-2,4,10-trioxatetracyclo<6.3.1.03,7.09,11>dodecane (137956-43-5,138052-10-5)

Guidance literature:

With Amberlyst 15; 4 A molecular sieve; In acetonitrile; for 1h; Ambient temperature;

DOI:10.1016/S0040-4020(01)82332-2

Reference yield:

(1S,4S,5S)-5-Bromobicyclo<2.2.1>heptan-2-one (128111-35-3) → (1S,3R,5RS,7S,8R,9S,11S)-7-(tert-Butyldimethylsilyloxy)-5-phenylseleno-2,4,10-trioxatetracyclo<6.3.1.03,7.09,11>dodecane (137956-43-5,138052-10-5)

Guidance literature:

Multi-step reaction with 15 steps

1: 92 percent / pyridinium p-toluenesulphonate / benzene / 3 h / Heating

2: 81 percent / potassium superoxide, 18-crown-6 / dimethylsulfoxide; 1,2-dimethoxy-ethane / 60 h / Ambient temperature; repeated addition of K₂O and 18-crown-6

3: 1.) sodium hydride, 2.) tetra-n-butylammonium iodide / 1.) THF, r.t., 30 min, 2.) r.t., 12 h

4: 1 M HCl / tetrahydrofuran / 2.75 h / 50 °C

5: 91 percent / m-chloroperbenzoic acid, p-toluenesulphonic acid monohydrate / CH₂Cl₂ / 1 h / Ambient temperature

6: 1.) lithium diisopropylamide, 2.) oxodiperoxymolybdenum(pyridine)-1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 1.) THF, hexane, -78 deg C, 1 h, 2.) -78 deg C, 15 min, then -30 to -20 deg C, 30 min, then to r.t.

7: imidazole / dimethylformamide / 14 h / Ambient temperature

8: 1a.) potassium diisopropylamide, 1b.) HMPA / 1.) THF, hexane, -78 deg C, 2.) -78 to 0 deg C

10: 83 percent / 3 Angstroem molecular sieves, Amberlyst 15 / acetonitrile / 0.25 h / Ambient temperature

11: 98 percent / hydrogen, 1 M HCl / 10 percent Pd/C / methanol / 1 h / Ambient temperature

12: 99 percent / triethylamine / CH₂Cl₂ / 0.17 h / Ambient temperature

13: 1,8-diazabicyclo<5.4.0>undec-7-ene / toluene / 38 h / 120 °C

14: 99 percent / dimethyldioxirane / CH₂Cl₂; acetone / 14 h / Ambient temperature

15: 44 percent / Amberlyst 15, 4 Angstroem molecular sieves / acetonitrile / 1 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium superoxide; Amberlyst 15; 18-crown-6 ether; oxodiperoxymolybdenum(pyridine)-1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 3 A molecular sieve; 4 A molecular sieve; hydrogen; 3,3-dimethyldioxirane; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium diisopropylamide; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; benzene;

DOI:10.1016/S0040-4020(01)82332-2

Reference yield:

(1S,2S,4S,5S)-5-Bromobicyclo<2.2.1>heptan-2-ol (138125-10-7) → (1S,3R,5RS,7S,8R,9S,11S)-7-(tert-Butyldimethylsilyloxy)-5-phenylseleno-2,4,10-trioxatetracyclo<6.3.1.03,7.09,11>dodecane (137956-43-5,138052-10-5)

Guidance literature:

Multi-step reaction with 16 steps

1: 83 percent / tetra-n-propylammonium perruthenate, N-methylmorpholine-N-oxide, 4 Angstroem molecular sieves / acetonitrile / 12 h / Ambient temperature

2: 92 percent / pyridinium p-toluenesulphonate / benzene / 3 h / Heating

3: 81 percent / potassium superoxide, 18-crown-6 / dimethylsulfoxide; 1,2-dimethoxy-ethane / 60 h / Ambient temperature; repeated addition of K₂O and 18-crown-6

4: 1.) sodium hydride, 2.) tetra-n-butylammonium iodide / 1.) THF, r.t., 30 min, 2.) r.t., 12 h

5: 1 M HCl / tetrahydrofuran / 2.75 h / 50 °C

6: 91 percent / m-chloroperbenzoic acid, p-toluenesulphonic acid monohydrate / CH₂Cl₂ / 1 h / Ambient temperature

7: 1.) lithium diisopropylamide, 2.) oxodiperoxymolybdenum(pyridine)-1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 1.) THF, hexane, -78 deg C, 1 h, 2.) -78 deg C, 15 min, then -30 to -20 deg C, 30 min, then to r.t.

8: imidazole / dimethylformamide / 14 h / Ambient temperature

9: 1a.) potassium diisopropylamide, 1b.) HMPA / 1.) THF, hexane, -78 deg C, 2.) -78 to 0 deg C

11: 83 percent / 3 Angstroem molecular sieves, Amberlyst 15 / acetonitrile / 0.25 h / Ambient temperature

12: 98 percent / hydrogen, 1 M HCl / 10 percent Pd/C / methanol / 1 h / Ambient temperature

13: 99 percent / triethylamine / CH₂Cl₂ / 0.17 h / Ambient temperature

14: 1,8-diazabicyclo<5.4.0>undec-7-ene / toluene / 38 h / 120 °C

15: 99 percent / dimethyldioxirane / CH₂Cl₂; acetone / 14 h / Ambient temperature

16: 44 percent / Amberlyst 15, 4 Angstroem molecular sieves / acetonitrile / 1 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium superoxide; Amberlyst 15; tetrapropylammonium perruthennate; 18-crown-6 ether; oxodiperoxymolybdenum(pyridine)-1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 3 A molecular sieve; 4 A molecular sieve; hydrogen; 3,3-dimethyldioxirane; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium diisopropylamide; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; benzene;

DOI:10.1016/S0040-4020(01)82332-2

upstream raw materials:

Benzeneselenol

(1S,3R,5RS,7S,8R,9S,11S)-7-(tert-Butyldimethylsilyloxy)-5-methoxy-2,4,10-trioxatetracyclo<6.3.1.0^3,7.0^9,11>dodecane

(1S,4S,5S)-5-Bromobicyclo<2.2.1>heptan-2-one

(1S,2S,4S,5S)-5-Bromobicyclo<2.2.1>heptan-2-ol