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CAS No. : | 572924-54-0 | MDL No. : | MFCD13184816 |
Formula : | C53H84NO14P | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 990.21 | Pubchem ID : | - |
Synonyms : |
Deforolimus;AP23573;Deforolimus, Ridaforolimus;MK-8669
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.84 g | With sulfuric acid; water In tetrahydrofuran at -5 - 0℃; | 42-(dimethylphosphinate)-31-triethylsilylether Rapamycin (VI-b) (2.312 g, available from 1.945 mmole of Rapamycin -28-triethylsilylether) and tetrahydrofuran (60 mL) was placed into a flask, and the resulting solution was cooled to 0−5° C. Next, a sulthric acid solution (2 N, 6 mL) was slowly added into the resulting solution dropwise. When the 42-(dimethylphosphinate)-31-triethylsilylether Rapamycin (VI-b) was less than 2percent, ethyl acetate (1000 mL) was added into the resulting solution. Then, the organic layer was successively washed with a NaCl saturated solution (300 mL), a NaHCO3 saturated solution (200 mL) and a NaCl saturated solution (200 mL), dried over anhydrous sodium sulfate and concentrated to obtain a crude product of 42-(dimethylphosphinate) Rapamycin (Ridaforolimus) (I) (2.341 g). The crude product was then purified by Licrhoprep RP-18 silica gel chromatography (eluted with acetonitrile: 0.02 M ammonium formate solution=6:4, wherein the pH of the ammonium formate solution was adjusted to 4.0 with formic acid), extracted with ethyl acetate, concentrated and dried to obtain a white foam solid 42-(dimethylphosphinate) Rapamycin (Ridaforolimus) (I) (1.840 g, purity=99.48percent). The yield thereof was 95.55percent based on 2.0 g of 31-triethylsilyl ether Rapamycin. 1H-NMR(400 MHz, CDCl3)d 4.18(m, 1H), 4.10(m, 1H), 3.05(m, 1H),1.51(m, 6H); 31P-NMR(161 MHz, CDCl3)d 53.33; 1012.6 m/z [M+Na]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81.03 %Chromat. | Stage #1: With 3,5-Lutidine In dichloromethane at 0 - 5℃; for 1.08333 h; Inert atmosphere Stage #2: at 0 - 5℃; for 1 h; Inert atmosphere |
To a flask containing 31-trimethylsilylether Rapamycin (V-a) (300 mg, 0.304 mmole) was added dichloromethane (2 mL) under a stream of N2(g). The resulting solution was stirred until 31-trimethylsilylether Rapamycin (V-a) was completely dissolved and cooled to 0-5° C. Next, a mixture of 3,5-lutidine (72 mg, 0.67 mmole) and dichloromethane (1 mL) was added therein dropwise over a period of more than 5 min. Then, a mixture of dimethylphosphinic chloride (DMP-Cl) (144 mg, 1.22 mmole) and dichloromethane (1 mL) was added therein dropwise over a period of more than 5 min. The resulting solution was kept at 0-5° C. for 1 hr, and monitored with HPLC. To the resulting solution was added ethyl acetate (40 mL) dropwise, followed by ethyl acetate until the final volume thereof was 300 mL. The resulting solution was successively washed with a NaHCO3 saturated solution (100 mL), an iced HCl solution (0.5 N. 100 mL), a NaHCO3 saturated solution (100 mL) and a NaCl saturated solution (100 mL), then the organic layer was dried over anhydrous sodium sulfate and concentrated to obtain a crude product of 42-(dimethylphosphinate) Rapamycin (Ridaforolimus) (I) (314 mg). The HPLC analysis data indicated that the crude product contained 81.03percent (area percent) of 42-(dimethylphosphinate) Rapamycin (Ridaforolimus) (I), 5.14percent of Rapamycin (II), 0.54percent of 31,42-bis(dimethyl phosphinate) Rapamycin (III), and 2.5percent of 42-(dimethylphosphinate)-31-trimethylsilylether Rapamycin (VI-a). |