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Chemical Structure| 58-97-9
Chemical Structure| 58-97-9
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Product Details of [ 58-97-9 ]

CAS No. :58-97-9 MDL No. :MFCD00067346
Formula : C9H13N2O9P Boiling Point : -
Linear Structure Formula :- InChI Key :DJJCXFVJDGTHFX-XVFCMESISA-N
M.W : 324.18 Pubchem ID :6030
Synonyms :
5'-​Uridylic acid;UMP;Uridine monophosphate;58-97-9;Uridylic acid;5'-URIDYLIC ACID;5′-UMP

Safety of [ 58-97-9 ]

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:

Application In Synthesis of [ 58-97-9 ]

* 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.

  • Upstream synthesis route of [ 58-97-9 ]
  • Downstream synthetic route of [ 58-97-9 ]

[ 58-97-9 ] Synthesis Path-Upstream   1~38

  • 1
  • [ 56428-57-0 ]
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  • [ 3803-29-0 ]
YieldReaction ConditionsOperation in experiment
76.3% at 25℃; General procedure: 15mM solutions of selected activated nucleotides, ImpN (N = A, U, C, G, dA)2 were dissolved in 1M sodium fluoride (Sigma). The reaction mixtures were allowed to stand at 24 °C for 8-10 days with periodic monitoring by HPLC using a reverse phase column. After completion of the reaction, each product mixture comprised the corresponding phosphorofluoridate together with a small amount of the NMP hydrolysis product. The materials were separated using a semi-preparative reverse phase Alltima C-18, 5 (10 mm x 300 mm)column (Alltech, Grace Davison) under isocratic conditions (88percent of 0.2percent aqueous formic acid (Sigma) and 12percent of 30percent acetonitrile in water with 0.2percent formic acid) at flow rate of mL/minute. The individual samples collected were analyzed by mass spectrometry.
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 8, p. 1464 - 1466
  • 2
  • [ 362-43-6 ]
  • [ 58-97-9 ]
Reference: [1] Journal of Biological Chemistry, 1934, vol. 106, p. 113,115, 118
[2] Zeitschrift fuer Naturforschung, 1962, vol. 17b, p. 291,293
[3] Journal of the Chemical Society, 1949, p. 2476,2484
[4] Journal of the American Chemical Society, 1954, vol. 76, p. 5056,5058
[5] Journal of the American Chemical Society, 1955, vol. 77, p. 1871,1872, 1873
[6] Journal of the Chemical Society, 1958, p. 1957,1961
[7] Organic Letters, 2005, vol. 7, # 10, p. 1999 - 2002
[8] Tetrahedron Letters, 1987, vol. 28, # 20, p. 2259 - 2262
[9] Patent: DE1119278, 1958, ,
  • 3
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  • [ 26184-65-6 ]
YieldReaction ConditionsOperation in experiment
7.2 mg at 20℃; for 48 h; The mixture containing compound 7 (16.3 mg, 44.0 μmol) was co-evaporated with pyridine (3 × 1.0 mL) and dissolved in pyridine (1.0 mL). The solution was added to UMP-morpholidate (43.5 mg, 63.4 μmol), which evaporated with pyiridine (3 × 1.0 mL), in the reaction flask. Moreover, 1H-tetrazole (9.9 mg, 142 μmol) was co-evaporated with pyridine (3 × 1.0 mL) and dissolved in pyridine (300 μL). The solution was transferred to the reaction flask by a syringe and the mixture was then stirred at room temperature for 48 h. The mixture was evaporated and the residue was purified by silica gel chromatography with 7:1 (v/v/v) acetonitrile:water. The absorbance of each fraction was measured at 262 nm and the combined fractions were evaporated. The residue was purified by silica gel chromatography with 7:3:1 (v/v/v) ethyl acetate:methanol:water to give 9 (7.2 mg, 31percent) as a syrup: Rf 0.38 (acetonitrile:water = 4:1) ; 1H NMR δ (D2O, 400 MHz) 8.02 (d, 1H, J5'', 6'' = 2.8 Hz, H-6''), 5.99-5.96 (m, 2 H, H-1', H-5''), 5.76 (br-d, 1 H, J1, 2eq = 4.4 Hz, H-1), 5.31 (m, 1 H, J2eq, 3 = 5.6 Hz, J3, 4 = 9.6 Hz, H-3), 4.97 (t, 1 H, H-4), 4.45 (dd, 1 H, J5, 6a = 2.8 Hz, J6a, 6b = 12.4 Hz, H-6a), 4.36-4.18 (m, 6 H, H-2', 3', 4', 5, 5'), 4.11 (dd, 1 H, J5, 6b = 2.0 Hz, H-6b), 2.38 (br-dd, 1 H, J2ax, 2eq = 13.0 Hz, H-2eq), 2.10-1.99 (m, 9 H, Acetyl × 3), 1.99-1.90 (m, 1 H, H-2ax); 13C NMR δ (D2O, 100 MHz) 173.74 (4C, C=O), 173.32, 173.14, 166.15 (C-4''), 151.71 (C-2''), 141.72 (C-6''), 102.52 (C-5''), 94.18 (C-1), 88.62 (C-1'), 83.00 (C-4'), 73.96 (C-2'), 69.38-68.60 (C-3, 3', 4, 5), 65.93 (C-5'), 61.94 (C-6), 34.64 (C-2), 20.32 (3C, CH3), 20.14, 20.08; 31P NMR δ (D2O, 162 MHz) -10.36 (m, 1P, P-2), -12.70 (m, 1P, P-1); ESI-HRMS m/z calcd for C21H29N2O19P2- [M-H]-: 675.0845, found: 675.0858.
Reference: [1] Synthetic Communications, 2016, vol. 46, # 22, p. 1790 - 1795
  • 4
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YieldReaction ConditionsOperation in experiment
19.7 mg at 20℃; for 48 h; The mixture containing compound 8 (21.8 mg, 58.9 μmol) was co-evaporated with pyridine (3 × 1.0 mL) and dissolved in pyridine (1.0 mL). The solution was added to UMP-morpholidate (80.9 mg, 118 μmol) which evaporated with pyiridine (3 × 1.0 mL) in the reaction flask. Moreover, 1H-tetrazole (15.7 mg, 224 μmol) was co-evaporated with pyridine (3 × 1.0 mL) and dissolved in pyridine (300 μL), then the solution was transferred to the reaction flask by a syringe. The mixture was stirred at room temperature for 48 h. The mixture was evaporated and the residue was purified by silica gel chromatography with 7:1 (v/v/v) acetonitrile:water. The absorbance of each fraction was measured at 262 nm and the combined fractions were evaporated. The residue was purified by silica gel chromatography with 7:3:1 (v/v/v) ethyl acetate:methanol:water to give 10 (19.7 mg, 50percent) as a syrup: Rf 0.42 (acetonitrile:water = 4:1); 1H NMR δ (D2O, 400 MHz) 7.98 (d, 1H, J5'', 6'' = 8.0 Hz, H-6''), 5.98-5.94 (m, 2 H, H-1', H-5''), 5.83 (br-d, 1 H, J1, P = 9.8 Hz, H-1), 5.37 (s, 1 H, H-4), 5.28 (qd, 1 H, H-3), 4.51 (br-t, 1 H, J5, 6a = 6.0 Hz, H-5), 4.36-4.32 (m, 2 H, H-2', H-3'), 4.27-4.11 (m, 5 H, H-4', 5', 6a, 6b), 2.21-1.99 (m, 11 H, H-2eq, H-2ax, acetyl-H×3); 13C NMR δ (D2O, 100 MHz) 174.06 (3C, C=O), 173.97, 173.35, 166.55 (C-4''), 152.11 (C-2''), 142.07 (C-6''), 102.93 (C-5''), 95.17 (C-1), 89.12 (C-1'), 83.36 (C-4'), 74.30 (C-2', C-3'), 69.83, 67.91 (C-3), 67.57 (C-5), 66.91 (C-4), 65.24 (C-5'), 62.73 (C-6), 30.32 (C-2), 20.67 (3C, CH3), 20.57, 20.45; 31P NMR δ (D2O, 162 MHz) -10.34 (m, 1P, P-2), -12.62 (m, 1P, P-1); ESI-HRMS m/z calcd for C21H29N2O19P2- [M-H]-: 675.0845, found: 675.0855.
Reference: [1] Synthetic Communications, 2016, vol. 46, # 22, p. 1790 - 1795
  • 5
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  • 26
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  • 29
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