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CAS No. : | 58-58-2 | MDL No. : | MFCD00012691 |
Formula : | C22H31Cl2N7O5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MKSVFGKWZLUTTO-FZFAUISWSA-N |
M.W : | 544.43 | Pubchem ID : | 443311 |
Synonyms : |
CL13900 dihydrochloride;Puromycin (hydrochloride);PDH;NSC 3055;CL 16,536;CL 13,900;CL13900 2HCl;Puromycin 2HCl
|
Chemical Name : | (S)-2-Amino-N-((2S,3S,4R,5R)-5-(6-(Dimethylamino)-9H-purin-9-yl)-4-hydroxy-2-(hydroxymethyl)tetrahydrofuran-3-yl)-3-(4-methoxyphenyl)propanamide dihydrochloride |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P264-P270-P301+P312+P330-P501 | UN#: | N/A |
Hazard Statements: | H302 | Packing Group: | N/A |
GHS Pictogram: |
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* 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 |
---|---|---|
75% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 18h; | A mixture of puromycin dihydrochloride (50 mg, 0.092 mmol) , Oi-Boc-Lys (epsilon-Ac) -OH (31 mg, 0.11 mmol) , EDC-HC1 (21 mg, 0.11 mmol), HOBt-H20 (17 mg, 0.11 mmol), and DIEA (N,N- diisopropylethylamine) (18 ]1L, 0.11 mmol) was stirred in DMF (10 ml) at rt for 18 h. After concentrating the solution under reduced pressure, the residue was dissolved in DCM. The DCM solution was washed with 0 three times, dried over Na2S04, and concentrated. The crude oil was purified by silica gel column chromatography using a linear gradient from 5 to 10 % MeOH in DCM and dried to yield a-Boc-Lys ( E-AC) -Puromycin as a white solid (55 mg, 75 % yield) : mp: 182-183 C; NMR (500 MHz, DMSO) delta 8.43 (s, 1H, H-29) , 8.22 (s, 1H, H-32), 8.15 (d, J = 1.1 Hz, 1H, H-8'), 7.74 (d, J = 7.1 Hz, 2H, Eta-2', H-23'), 7.15 (d, J = 8.4 Hz, 2H, H-17), 6.86 (d, J = 8.3 Hz,' 1H, H-9'), 6.80 (d, J = 8.6 Hz, 2H, H-16, H-20), 6.03 (d, J = 4.6 Hz, 1H, H-28), 5.98 (d, J = 2.8 Hz, 1H, H-27) , 5.18 (t, J = 5.4 Hz, 1H, H-22), 4.60 (dd, J - 13.6, 8.1 Hz, 1H, H-7), 4.52 - 4.39 (m, 2H, H-25, H-26), 3.98 - 3.76 (m, 2H, H-24), 3.70 (s, 3H, H-14) , 3.69 -3.40 (m, 6H, H-34, H-35), 3.02 - 2.86 (m, 3H, H-3, H-21) , 2.76 (dd, J = 13.7, 8.7 Hz, 1H, H-21), 1.77 (s, 3H, H-l) , 1.52 - 1.38 (m, 2H, H-6), 1.38 - 1.32 (s, 9H, H-ll, H-12, H-13), 1.33 - 1.05 (ra, 6H, H-4, H-5) ppm. 13C NMR (101 MHz, DMSO) delta 169.5 (C-8, C-23), 158.4 (C-9), 155.8 (C-2), 154.8 (C-33), 152.4 (C-32), 150.2 (C-31) , 138.4 (C-29), 138.3 (C-15), 131.0 (C-17, C-19), 129.8 (C-18) , 120.2 (C- 30), 114.0 (C-16, C-20), 90.0 (C-28) , 78.8 (C-10, C-25) , 73.8 (C- 27), 61.5 (C-24), 55.6 (C-26) , 55.3 (C-7), 54.5 (C-22), 51.0 (C- 14), 40 ( (C-34, C-35, underneath DMSO peak), 39.1 (C-3), 38.2 (C- 21), 32.5 (C-6), 29.5 (C-4) , 28.9 (C-ll, C-12, C-13), 23.7 (C-5) , 23.4 (C-l); MS (ifl/z) : [M] + calcd. for C35H51N9O9, 742.38; found, 742.47. |
75% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 18h; | A mixture of 15 puromycin dihydrochloride (50 mg, 0.092 mmol), 16 alpha-Boc-Lys(epsilon-Ac)-OH (31 mg, 0.11 mmol), 17 EDC.HCl (21 mg, 0.11 mmol), HOBt.H2O (17 mg, 0.11 mmol), and 18 DIEA (N,N-diisopropylethylamine) (18 muL, 0.11 mmol) was stirred in 19 DMF (10 ml) at rt for 18 h. After concentrating the solution under reduced pressure, the residue was dissolved in 20 DCM. The DCM solution was washed with H2O three times, dried over Na2SO4, and concentrated. The crude oil was purified by silica gel column chromatography using a linear gradient from 5 to 10% 21 MeOH in DCM and dried to yield alpha-Boc-Lys(s-Ac)-Puromycin as a white solid (55 mg, 75% yield): mp: 182-183 C.; 1H NMR (500 MHz, DMSO) delta 8.43 (s, 1H, H-29), 8.22 (s, 1H, H-32), 8.15 (d, J=7.7 Hz, 1H, H-8?), 7.74 (d, J=7.1 Hz, 2H, H-2?, H-23?), 7.15 (d, J=8.4 Hz, 2H, H-17), 6.86 (d, J=8.3 Hz, 1H, H-9?), 6.80 (d, J=8.6 Hz, 2H, H-16, H-20), 6.03 (d, J=4.6 Hz, 1H, H-28), 5.98 (d, J=2.8 Hz, 1H, H-27), 5.18 (t, J=5.4 Hz, 1H, H-22), 4.60 (dd, J=13.6, 8.1 Hz, 1H, H-7), 4.52-4.39 (m, 2H, H-25, H-26), 3.98-3.76 (m, 2H, H-24), 3.70 (s, 3H, H-14), 3.69-3.40 (m, 6H, H-34, H-35), 3.02-2.86 (m, 3H, H-3, H-21), 2.76 (dd, J=13.7, 8.7 Hz, 1H, H-21), 1.77 (s, 3H, H-1), 1.52-1.38 (m, 2H, H-6), 1.38-1.32 (s, 9H, H-11, H-12, H-13), 1.33-1.05 (m, 6H, H-4, H-5) ppm. 13C NMR (101 MHz, DMSO) delta 169.5 (C-8, C-23), 158.4 (C-9), 155.8 (C-2), 154.8 (C-33), 152.4 (C-32), 150.2 (C-31), 138.4 (C-29), 138.3 (C-15), 131.0 (C-17, C-19), 129.8 (C-18), 120.2 (C-30), 114.0 (C-16, C-20), 90.0 (C-28), 78.8 (C-10, C-25), 73.8 (C-27), 61.5 (C-24), 55.6 (C-26), 55.3 (C-7), 54.5 (C-22), 51.0 (C-14), 40 ((C-34, C-35, underneath DMSO peak), 39.1 (C-3), 38.2 (C-21), 32.5 (C-6), 29.5 (C-4), 28.9 (C-11, C-12, C-13), 23.7 (C-5), 23.4 (C-1); MS (m/z): [M]+ calcd. for C35H51N9O9, 742.38; found, 742.47. |