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ChemicalBook CAS DataBase List Ursolic acid
77-52-1

Ursolic acid synthesis

5synthesis methods
Urs-12-en-28-oic acid, 3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-, (1,1-dimethylethyl)diphenylsilyl ester, (3β)-

1381876-19-2

Ursolic acid

77-52-1

GENERAL METHODS: TBDPS ether (1.0 mmol) was dissolved in acetonitrile (5.0 mL), followed by the addition of trifluoromethanesulfonic acid silica gel (TfOH-SiO2, 50 mg, 0.1 mmol). The resulting non-homogeneous mixture was stirred at 50 °C and the reaction progress was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the mixture was filtered and the solid residue was washed with acetonitrile. The filtrates were combined, the solvent was removed by concentration under reduced pressure, and the resulting residue was purified by column chromatography to give the target product ursolic acid.

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Yield:77-52-1 73%

Reaction Conditions:

with perchloric acid on silica gel in acetonitrile at 50; for 0.5 h;chemoselective reaction;

Steps:

4.5. Procedure C: Typical experimental protocol for the deprotection of TBDPS ethers catalyzed by TfOH-SiO2

General procedure: To a solution of TBDPS ether (1.0 mmol) in CH3CN (5.0 mL) was added TfOH-SiO2 (50 mg, 0.1 mmol). The heterogeneous mixture was stirred at 50 °C and the reaction was followed by TLC. After completion, the mixture was filtered and washed with CH3CN. The combined filtrate was concentrated under vacuum and the residue was purified by column chromatography to obtain the pure product.

References:

Yan, Shiqiang;Ding, Ning;Zhang, Wei;Wang, Peng;Li, Yingxia;Li, Ming [Carbohydrate Research,2012,vol. 354,p. 6 - 20] Location in patent:experimental part

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