ChemicalBook CAS DataBase List 40-O-[2-(t-butyldimethylsilyl)oxy]ethyl rapamycin

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

6synthesis methods

Product Name:40-O-[2-(t-butyldimethylsilyl)oxy]ethyl rapamycin
CAS Number:159351-68-5
Molecular formula:C59H97NO14Si
Molecular Weight:1072.5

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Trifluoromethanesulfonic acid tert-butyldimethylsilyl ester

69739-34-0
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53123-88-9 Synthesis

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

159351-68-5
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Yield:159351-68-5 76 %Chromat.

Reaction Conditions:

Stage #1:oxirane;t-butyldimethylsiyl triflate with N-ethyl-N,N-diisopropylamine in toluene at 20; for 0.666667 h;
Stage #2:sirolimus with N,N-diisopropylethylamine trifluoromethanesulfonate in 1,2-dimethoxyethane;toluene at 48 - 50; for 18 h;Inert atmosphere;

Steps:

1 Example 1 : Synthesis of 40-O-[2-(f-butyldimethylsilyl)oxy]ethyl-rapamycin
Example 1 : Synthesis of 40-O-[2-(f-butyldimethylsilyl)oxy]ethyl-rapamycin A mixture of 7.9 ml of 1 M ethylene oxide solution in toluene and 1.01 g of Λ/,/ν-diisopropyl- ethylamine was added under stirring to 1.72 g of f-butyldimethylsilyl trifluoromethane- sulfonate. The resulting mixture was stirred for further 40 min at 20°C. Then, 0.66 ml of 1 ,2- dimethoxyethane and 1.82 g of W,/v-diisopropylethylamine trifluoromethanesulfonate were added. The resulting mixture was stirred at 20°C until complete dissolution, before 1 .0 g of rapamycin was added. The reaction mixture was purged with nitrogen for 10 min, heated to 48-50°C and stirred at this temperature for 18 h. Subsequently, the reaction mixture was cooled to 20°C, and 0.2 ml of pyridine and 16 ml of heptane were added. The resulting mixture was stirred for 10 minutes. The precipitate formed was obtained by filtration and washed with a mixture of 4.0 ml of toluene and 9.4 ml of heptane. Then, 1 ml of 0.2% solution of 2,6-di-f-butyl-4-methylphenol in heptane was added to the filtrate and the resulting crude 40-O-[2-(f-butyldimethylsilyl)oxy]ethyl-rapamycin solution was subjected to the deprotection step. HPLC analysis of the obtained 40-O-[2-(f-butyldimethylsilyl)oxy]ethyl- rapamycin solution showed an overall yield of 76% (895 mg).

References:

SYNBIAS PHARMA AG;ZABUDKIN, Oleksandr;SCHICKANEDER, Christian;MATVIIENKO, Iaroslav;SYPCHENKO, Volodymyr WO2016/207205, 2016, A1 Location in patent:Page/Page column 12; 13

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53123-88-9 Synthesis

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