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(1S,3R,5RS,7S,8R,9R)-7-(tert-Butyldimethylsilyloxy)-5-phenylseleno-2,4-dioxatricyclo<6.2.1.03,7>undecan-9-ol methanesulphonate

Base Information Edit
  • Chemical Name:(1S,3R,5RS,7S,8R,9R)-7-(tert-Butyldimethylsilyloxy)-5-phenylseleno-2,4-dioxatricyclo<6.2.1.03,7>undecan-9-ol methanesulphonate
  • CAS No.:137956-70-8
  • Molecular Formula:C22H34O6SSeSi
  • Molecular Weight:533.62
  • Hs Code.:
  • Mol file:137956-70-8.mol
(1S,3R,5RS,7S,8R,9R)-7-(tert-Butyldimethylsilyloxy)-5-phenylseleno-2,4-dioxatricyclo<6.2.1.0<sup>3,7</sup>>undecan-9-ol methanesulphonate

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Chemical Property of (1S,3R,5RS,7S,8R,9R)-7-(tert-Butyldimethylsilyloxy)-5-phenylseleno-2,4-dioxatricyclo<6.2.1.03,7>undecan-9-ol methanesulphonate Edit
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Technology Process of (1S,3R,5RS,7S,8R,9R)-7-(tert-Butyldimethylsilyloxy)-5-phenylseleno-2,4-dioxatricyclo<6.2.1.03,7>undecan-9-ol methanesulphonate

There total 14 articles about (1S,3R,5RS,7S,8R,9R)-7-(tert-Butyldimethylsilyloxy)-5-phenylseleno-2,4-dioxatricyclo<6.2.1.03,7>undecan-9-ol methanesulphonate 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:
Guidance literature:
Multi-step reaction with 12 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
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; 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; benzene;
DOI:10.1016/S0040-4020(01)82332-2
Guidance literature:
Multi-step reaction with 13 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
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; 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; acetonitrile; benzene;
DOI:10.1016/S0040-4020(01)82332-2
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