(1S,3R,5RS,7S,8R)-7-(tert-Butyldimethylsilyloxy)-5-phenylseleno-2,4-dioxatricyclo<6.2.1.0^3,7>undec-9-ene

Base Information

• Chemical Name: (1S,3R,5RS,7S,8R)-7-(tert-Butyldimethylsilyloxy)-5-phenylseleno-2,4-dioxatricyclo<6.2.1.0^3,7>undec-9-ene
• CAS No.: 137956-52-6
• Molecular Formula: C₂₁H₃₀O₃SeSi
• Molecular Weight: 437.513
• Mol file: 137956-52-6.mol

Synonyms:

Chemical Property of (1S,3R,5RS,7S,8R)-7-(tert-Butyldimethylsilyloxy)-5-phenylseleno-2,4-dioxatricyclo<6.2.1.0^3,7>undec-9-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3R,5RS,7S,8R)-7-(tert-Butyldimethylsilyloxy)-5-phenylseleno-2,4-dioxatricyclo<6.2.1.0^3,7>undec-9-ene

There total 15 articles about (1S,3R,5RS,7S,8R)-7-(tert-Butyldimethylsilyloxy)-5-phenylseleno-2,4-dioxatricyclo<6.2.1.0^3,7>undec-9-ene 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: 78.0%

(1S,3R,5RS,7S,8R,9R)-7-(tert-Butyldimethylsilyloxy)-5-phenylseleno-2,4-dioxatricyclo<6.2.1.03,7>undecan-9-ol methanesulphonate (137956-70-8,138125-08-3) → (1S,3R,5RS,7S,8R)-7-(tert-Butyldimethylsilyloxy)-5-phenylseleno-2,4-dioxatricyclo<6.2.1.03,7>undec-9-ene (137956-52-6,138052-20-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; for 21h; Heating;

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)-7-(tert-Butyldimethylsilyloxy)-5-phenylseleno-2,4-dioxatricyclo<6.2.1.03,7>undec-9-ene (137956-52-6,138052-20-7)

Guidance literature:

Multi-step reaction with 13 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: 87 percent / hydrogen, HCl / 10 percent Pd/C / methanol / Ambient temperature

11: 60 percent / boron trifluoride etherate / CH₂Cl₂ / 0.17 h / 0 °C

12: 84 percent / triethylamine / CH₂Cl₂ / Ambient temperature

13: 78 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / toluene / 21 h / Heating

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium superoxide; 18-crown-6 ether; oxodiperoxymolybdenum(pyridine)-1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; boron trifluoride diethyl etherate; hydrogen; 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; toluene; 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)-7-(tert-Butyldimethylsilyloxy)-5-phenylseleno-2,4-dioxatricyclo<6.2.1.03,7>undec-9-ene (137956-52-6,138052-20-7)

Guidance literature:

Multi-step reaction with 14 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: 87 percent / hydrogen, HCl / 10 percent Pd/C / methanol / Ambient temperature

12: 60 percent / boron trifluoride etherate / CH₂Cl₂ / 0.17 h / 0 °C

13: 84 percent / triethylamine / CH₂Cl₂ / Ambient temperature

14: 78 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / toluene / 21 h / Heating

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium superoxide; tetrapropylammonium perruthennate; 18-crown-6 ether; oxodiperoxymolybdenum(pyridine)-1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; 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; toluene; acetonitrile; benzene;

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

upstream raw materials:

(1S,3R,5RS,7S,8R,9R)-7-(tert-Butyldimethylsilyloxy)-5-phenylseleno-2,4-dioxatricyclo<6.2.1.0^3,7>undecan-9-ol methanesulphonate

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

Benzeneselenol

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

Downstream raw materials:

(1S,3R,5RS,7S,8R,9R)-7-(tert-Butyldimethylsilyloxy)-5-phenylseleno-2,4-dioxatricyclo<6.2.1.0^3,7>undecan-9-ol