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Chemical Structure| 1019209-73-4 Chemical Structure| 1019209-73-4

Structure of 1019209-73-4

Chemical Structure| 1019209-73-4

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Product Details of [ 1019209-73-4 ]

CAS No. :1019209-73-4
Formula : C16H25BrO4
M.W : 361.27
SMILES Code : CC(OCC1=CC=C(COC(C)(OC)C)C(Br)=C1)(OC)C

Safety of [ 1019209-73-4 ]

Application In Synthesis of [ 1019209-73-4 ]

* 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 [ 1019209-73-4 ]

[ 1019209-73-4 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 1019209-73-4 ]
  • [ 1461750-25-3 ]
  • ((1S,3'R,4'S,5'R,6'R)-3',4',5'-tri(benzyloxy)-6'-methyl-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-6-yl) methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
7.67 g Compound 52 1-9 (10.00 g, 27.68 mmol)was dissolved in anhydrous 26 tetrahydrofuran and 54 n-butyllithium (2.4 M in 55 hexane) (12.69 mL, 30.45 mmol) was added dropwise at -78 C under nitrogen. After the addition was completed and the mixture was stirred at -78 C for 1 hours, a solution of compound 43 1-6 (10.54 g, 24.36 mmol) in anhydrous tetrahydrofuran was added and the mixture was stirred for 2 hours at -78 C. TLC monitored (UV color) that the reaction was completed, then the reaction was transferred to room temperature and an appropriate amount of 56 water was added. After the reaction was warmed to room temperature, the mixture was extracted with ethylacetate, washed twice with saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated. The crude product was directly used in the next reaction. The crude product of the previous step was dissolved in 150mL of 57 tetrahydrofuran-methanol (tetrahydrofuran/methanol 2/1, v/v) and 58 p-toluenesulfonic acid (5.24 g, 30.45 mmol) was added at room temperature. After the addition was completed, the mixture was stirred at room temperature for 15 hours. TLC monitored (UV color) that the reaction was completed, then the reaction solution was concentrated to remove most of the methanol and extracted with ethylacetate. The combined organic layer was washed twice with saturated sodium bicarbonate solution, twice with saturated sodium chloride solution, dried over anhydrous sodium sulfate. After concentration, the crude product was isolated and purified by silica gel column chromatography (petroleum ether / ethylacetate 4/1, v/v) to give 7.67g 59 1-10 as a colorless oil in 57% yield (two consecutive steps). LRMS (ESI, m/z): 553 [M+H]+
  • 2
  • [ 1019209-73-4 ]
  • [ 1461750-25-3 ]
  • C35H36O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% To a solution of compound 52 (10.00g, 27.68mmol) in anhydrous THF (100mL), 2.4M n-BuLi in hexane solution (12.69mL, 30.45mmol) was added dropwise at-78C under a nitrogen atmosphere and the resultant mixture was stirred under the same condition for 1h. A solution of compound 49 (10.54g, 24.36mmol) in anhydrous THF (50mL) was then added dropwise to the resultant mixture. The reaction mixture was stirred for 2h, and then water was added thereto. The resultant mixture was extracted with EtOAc. The resultant organic layer was washed with water and brine and then dried over Na2SO4. The solvent was then removed by distillation under reduced pressure. The obtained residue was dissolved in a mixed solvent of THF (100mL) and MeOH (50mL), and p-toluenesulfonic acid (5.24g, 30.45mmol) was added thereto. The mixture was stirred at rt for 15h. After most of the MeOH was evaporated, the solution was extracted with EtOAc. The combined organic layer was washed with sat. aq. NaHCO3, brine, dried over Na2SO4, concentrated in vacuo, and purified by column chromatography on silica gel (petroleum ether/EtOAc=4/1) to give compound 53 (7.67g, 57%) as a colorless oil. LRMS (ESI, m/z): 553 [M+H]+.
 

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