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Chemical Structure| 73968-62-4 Chemical Structure| 73968-62-4

Structure of 73968-62-4

Chemical Structure| 73968-62-4

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Product Details of [ 73968-62-4 ]

CAS No. :73968-62-4
Formula : C24H22O3
M.W : 358.43
SMILES Code : O=C1O[C@H](COC(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4)CC1
MDL No. :MFCD00066260

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Application In Synthesis of [ 73968-62-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 73968-62-4 ]

[ 73968-62-4 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 1700-31-8 ]
  • [ 73968-62-4 ]
  • (R)-3-(3-benzyloxybenzyl)-4-butanolide [ No CAS ]
  • 2
  • [ 1700-31-8 ]
  • [ 73968-62-4 ]
  • C38H34O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
To tetrahydrofuran solution (200mL) of lithium diisopropylamide (0.092mol) cooledto -70 , a tetrahydrofuran solution (150mL) of (S) -5-trityloxy-4-pentanolide (30g, 0.084mol) obtained from L- glutamic acid by the method of previously reported (Tetrahedron, 30, pp.3547-3552 (1974)) was addeddropwise. After stirring for 30 min at -70 ° C, tetrahydrofuran solution (100mL) of 3- benzyloxybenzyl bromide (25.5g, 0.092mol) was allowed to react byadding dropwise. After stirring further at 70 for one hour, saturated aqueous solution of ammoniumchloride (250mL) and ethyl acetate (150mL) were added. The organic layer wasseparated and dried over anhydrous sodium sulfate, and then it was concentrated.After dissolving the residue in tetrahydrofuran (50 mL), tetrahydrofuran (10mL) suspension solution of ice-cooled lithium aluminum hydride (2.37 g, 0.063mol) was added and the lactone ring was reductively cleaved. After stirring for30 minutes at room temperature, it was ice-cooled and, saturated aqueous solutionmagnesium sulfate (10 mL) and potassium carbonate (20 mg) were added, andstirred at room temperature for 30 minutes. After filtration, the filtrate wasconcentrated and the residue was dissolved in ethanol (150 mL), and concentratedhydrochloric acid (3 mL) was added and triphenylmethyl group which is aprotecting group was removed. After allowed to stand for 1 hour at roomtemperature, neutralization was done by using saturated aqueous solution ofsodium hydrogen carbonate and concentrated. After the residue was mixed byadding chloroform and water, the chloroform solution was separated and driedover anhydrous sodium sulfate. After further concentration, the residue waspurified by silica gel column (eluent: ethyl acetate / hexane = 3/1). Theresulting triol was dissolved in methanol (150 mL), and then sodium periodate(8.76 g, 0.041 mol) was added, and by stirring at room temperature for 1.5hours, 1,2-diol structure was cleaved once oxidatively, and then recircularizedby acetal reaction. After concentration, the residue was added to dichloromethaneand water, and mixed. The dichloromethane solution was separated and,concentrated after drying over anhydrous sodium sulfate, and the residue wasdissolved in dichloromethane (100 mL), and after adding molecular sieves (1 g),pyridinium chlorochromate (8.86 g, 0.041 mol) was added, and acetal ring was oxidized.After stirring for 12 hours at room temperature, ether was added and filtered.The filtrate was concentrated, and then the residue was purified by silica gelcolumn (eluent: ethyl acetate / hexane = 1/3) to obtain an oily (R)-3-(3-benzyloxybenzyl) -4-butanolide (7.97 g, 0.028mol, 5 steps overall yield: 33percent).
 

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