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CAS No. : | 232931-57-6 | MDL No. : | MFCD19443671 |
Formula : | C31H32N4O6 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RWZVMMQNDHPRQD-SFTDATJTSA-N |
M.W : | 556.61 | Pubchem ID : | 393111 |
Synonyms : |
NSC-694501
|
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 |
---|---|---|
70% | With lithium borohydride; ethanol In tetrahydrofuran for 1 h; Inert atmosphere | Solid bis-SEM-dilactam 8 (100 mg, 0.12 mmol) was dissolved in a mixture of ethanol (3 mL) and THF (3 ml_). Lithium borohydride (22 mg, 2.3 mmol) was added in one portion and the reaction mixture was allowed to stir for 1h under nitrogen. LC/MS revealed completion of the reaction. The reaction mixture was partitioned between water (35 mL) and chloroform (50 mL). The organic phase was washed with water (35 mL), brine (35 mL), dried over magnesium sulphate and concentrated by rotary evaporation under vacuum. The residue was redissolved in a mixture of chloroform (2 mL), ethanol (2 mL) and water (2.5 mL). Silica gel (4g) was added and the mixture was allowed to stir for 48h. The mixture was filtered through a sinter funnel and washed with a mixture of chloroform / methanol (90:10 v/v). The filtrate was extracted with chloroform, washed with brine, dried over magnesium sulphate and concentrated by rotary-evaporation under vacuum. The residue was purified by flash chromatography (gradient elution: 100percent CHCI3 to 97:3 v/v CHCI3/MeOH). The pure fractions were pulled and the solvent removed by rotary-evaporation under vacuum to give the desired product SJG-136 as a mixture of imine and carbinolamine methyl ethers. (46 mg, 70percent).Analytical Data: LC/MS 2.50 min (ES-) m/z (relative intensity) 555.06 ([M - H]-, 100); Analytical description identical to previously published by Gregson ef a/., J. Med. Chem. 2001 , 44, 1161-1174. However, the [O.]D value was found to be higher than reported: [α]20D = +766° (c = 0.37, HPLC CHCI3) (lit [α]20D = +358° (c = 0.07, CHCI3)). This was expected, as the optical rotation measurement is very sensitive to the chloroform purity and the ratio of imine / carbinolamine adducts |