ChemicalBook CAS DataBase List Everolimus

Everolimus synthesis

3synthesis methods

Product Name:Everolimus
CAS Number:159351-69-6
Molecular formula:C53H83NO14
Molecular Weight:958.22

Everolimus, also known as RAD001, is a derivative of the natural macrocyclic lactone sirolimus with immunosuppressant and anti-angiogenic properties. In cells, everolimus binds to the immunophilin FK Binding Protein-12 (FKBP-12) to generate an immunosuppressive complex that binds to and inhibits the activation of the mammalian Target of Rapamycin (mTOR), a key regulatory kinase. Inhibition of mTOR activation results in the inhibition of T lymphocyte activation and proliferation associated with antigen and cytokine (IL-2, IL-4, and IL-15) stimulation and the inhibition of antibody production.

Synthetic Routes

ROUTE 1

ROUTE 2

ROUTE 3

ROUTE 4

ROUTE 5

ROUTE 6

Polymer compositions containing a macrocyclic triene compound; Shulze, John E.; Betts, Ronald E.; Savage, Douglas R.; Assignee Sun Bow Co., Ltd., Bermuda; Sun Biomedical Ltd. 2003; Patent Information; Nov 06, 2003; WO 2003090684 A2

159351-68-5 Synthesis

40-O-[2-(t-butyldimethylsilyl)oxy]ethyl rapamycin

159351-68-5
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159351-69-6
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Yield:159351-69-6 98.1%

Reaction Conditions:

with hydrogenchloride in lithium hydroxide monohydrate;ethyl acetate at 0 - 5;Temperature;

Steps:

19-22 Example 19

At room temperature, compound V (9.64 g, 9 mmol) was added to 50 mL of ethyl acetate, stirred and dissolved, cooled to 05° C., and hydrochloric acid solution (6.75 mL, 6.75 mmol, 1.0 mol/L) was added dropwise, and stirred until the reaction was completed, 50 mL of saturated NaHCO solution was added to the reaction solution, and the solution was separated. The aqueous phase was extracted with 25 mL of ethyl acetate. The organic phases were combined. The organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to dryness to obtain everolimus. The crude product, the crude everolimus was dissolved in 20 mL of ethyl acetate, then 20 mL of anhydrous ether was added, stirred for 1 h, and then concentrated under reduced pressure until a solid was precipitated. The obtained solid was added to 20 mL of anhydrous ether, stirred for 30 min, and concentrated to dryness under reduced pressure. Everolimus was obtained, the yield was 98.1%, and the HPLC purity was 99.83%.

References:

CN114539288,2022,A Location in patent:Paragraph 0017; 0096-0106

75-21-8
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53123-88-9 Synthesis

53123-88-9
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159351-69-6
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References

1392400-31-5
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159351-69-6
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References

Everolimus Related Search:

Rapamycin BIS(T-BUTYLDIMETHYLSILOXY)ETHANE Ezetimibe Etoposide Exemestane Ethyl 1-methylpipecolinate