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Chemical Structure| 27908-36-7 Chemical Structure| 27908-36-7
Chemical Structure| 27908-36-7

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Product Details of UMP-morpholidate

CAS No. :27908-36-7
Formula : C13H20N3O9P
M.W : 393.29
SMILES Code : OP(N1CCOCC1)(OC[C@@H]2[C@@H](O)[C@@H](O)[C@]([H])(N3C=CC(NC3=O)=O)O2)=O
English Name :((2R,3S,4R,5R)-5-(2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl hydrogen morpholinophosphonate
MDL No. :N/A

Safety of UMP-morpholidate

Application In Synthesis of UMP-morpholidate

* 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.

  • Downstream synthetic route of [ 27908-36-7 ]

[ 27908-36-7 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 5574-97-0 ]
  • [ 27908-36-7 ]
  • [ 34819-86-8 ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
1: 52% 2: 50% Stage #1: 3,4-di-O-acetyl-1,5-anhydro-2,6-dideoxy-L-arabino-hex-1-enitol With hydrogenchloride In benzene at 20℃; for 0.5h; Stage #2: tetra-n-butylammonium dihydrogen phosphate With triethylamine In acetonitrile at 20℃; for 3h; Inert atmosphere; Molecular sieve; Stage #3: uridine 5'-monophosphate morpholidate Further stages; 1; 2; 3; 4; 5 Embodiment 1 first step synthesis general method General procedure: In a 25 mL round-bottomed flask, 1 g of acetylated glycal 1 was repeatedly dissolved in an appropriate amount of benzene for 3 times by rotary evaporation, and finally dissolved in 12 mL of benzene, and dried HCl (g) was poured into the reaction solution and stirred at room temperature. Reaction for 30min, TLC detects the reaction progress (petroleum ether: ethyl acetate=1:1), after the alkenose reaction is complete, HCl (g) and benzene are removed by distillation under reduced pressure to obtain a pale yellow syrupy mixture 2, which can be directly carried out next reaction. Embodiment 2 second step synthesis general method In a 50 mL round-bottomed flask, the mixture of 2 obtained above was dissolved in 25 mL of anhydrous CH3CN, the pH of the solution was adjusted to ≈ 9 with Et3N, the molecular sieves activated at high temperature were added, and the mixture was cooled in an ice-water bath. Dissolve 1.5g Bu4NH2PO4 in 12mL anhydrous CH3CN, under the protection of N2, add the Bu4NH2PO4 solution dropwise to the above 2 mixture, and the mixture reacts at room temperature for about 3h. The progress of the reaction was detected by TLC (with CH2Cl2:CH3OH:H2O:Et3N=16:8:0.2:0.3),After the reaction, the residual liquid was subjected to silica gel column chromatography with the system of CH2Cl2/CH3OH/H2O/Et3N=24/6/0.2/0.3 as eluent to obtain acetylated 2-deoxysugar-phosphate tetrabutylammonium salt 3. Embodiment 3 Synthesis general method of the third stepDissolve 0.05g of acetylated 2-deoxysugar-1-phosphate tetrabutylammonium salt 3 in a 25mL pear-shaped bottle, dissolve it with a small amount of anhydrous pyridine and rotate it, repeat 3 times, add 0.05g of UMP-morpholidate, and then add 0.01 g of UMP-morpholidate g tetrazole, finally added 0.5mL anhydrous pyridine as the reaction solvent, the whole reaction system was reacted under the protection of N2 gas for 48h, the reaction was detected by TLC, and the developing solvent was CHCl3:CH3OH:25%NH4OH:H2O=3.5:2:0.2:0.2 After the reaction, pyridine was evaporated, and pure uridine diphosphate acetylated-2-deoxysugar 4 was obtained by silica gel column chromatography (gradient elution with CHCl3:CH3OH:25% NH4OH:H2O system). The fourth step of embodiment 4 synthesis general method40.02g of uridine diphosphate acetylated-2-deoxysugar was dissolved in 2mL of CH3OH/H2O/Et3N (7/3/1) mixed solvent, reacted for 3h under stirring at room temperature, and the reaction progress was detected by TLC (with CHCl3:CH3OH: 25% NH4OH:H2O=1:1:0.2:0.2 system as a developing solvent), after the reaction, spin dry the solvent, and obtain uridine diphosphate 2-deoxysugar 5 in the form of triethylammonium salt by silica gel column chromatography . The acetyl group can also be removed by continuous reaction for 48 hours in a 25% NH4OH/H2O (1/5) solution system at 4°C.
  • 2
  • [ 5574-97-0 ]
  • [ 27908-36-7 ]
  • [ 34819-86-8 ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3,4-di-O-acetyl-1,5-anhydro-2,6-dideoxy-L-arabino-hex-1-enitol With hydrogenchloride In benzene at 20℃; for 0.5h; Stage #2: tetra-n-butylammonium dihydrogen phosphate With triethylamine In acetonitrile at 20℃; for 3h; Inert atmosphere; Molecular sieve; Stage #3: uridine 5'-monophosphate morpholidate With pyridine at 20℃; for 48h; Inert atmosphere; 1; 2; 3 Embodiment 1 first step synthesis general method General procedure: In a 25 mL round-bottomed flask, 1 g of acetylated glycal 1 was repeatedly dissolved in an appropriate amount of benzene for 3 times by rotary evaporation, and finally dissolved in 12 mL of benzene, and dried HCl (g) was poured into the reaction solution and stirred at room temperature. Reaction for 30min, TLC detects the reaction progress (petroleum ether: ethyl acetate=1:1), after the alkenose reaction is complete, HCl (g) and benzene are removed by distillation under reduced pressure to obtain a pale yellow syrupy mixture 2, which can be directly carried out next reaction. Embodiment 2 second step synthesis general method In a 50 mL round-bottomed flask, the mixture of 2 obtained above was dissolved in 25 mL of anhydrous CH3CN, the pH of the solution was adjusted to ≈ 9 with Et3N, the molecular sieves activated at high temperature were added, and the mixture was cooled in an ice-water bath. Dissolve 1.5g Bu4NH2PO4 in 12mL anhydrous CH3CN, under the protection of N2, add the Bu4NH2PO4 solution dropwise to the above 2 mixture, and the mixture reacts at room temperature for about 3h. The progress of the reaction was detected by TLC (with CH2Cl2:CH3OH:H2O:Et3N=16:8:0.2:0.3),After the reaction, the residual liquid was subjected to silica gel column chromatography with the system of CH2Cl2/CH3OH/H2O/Et3N=24/6/0.2/0.3 as eluent to obtain acetylated 2-deoxysugar-phosphate tetrabutylammonium salt 3. Embodiment 3 Synthesis general method of the third stepDissolve 0.05g of acetylated 2-deoxysugar-1-phosphate tetrabutylammonium salt 3 in a 25mL pear-shaped bottle, dissolve it with a small amount of anhydrous pyridine and rotate it, repeat 3 times, add 0.05g of UMP-morpholidate, and then add 0.01 g of UMP-morpholidate g tetrazole, finally added 0.5mL anhydrous pyridine as the reaction solvent, the whole reaction system was reacted under the protection of N2 gas for 48h, the reaction was detected by TLC, and the developing solvent was CHCl3:CH3OH:25%NH4OH:H2O=3.5:2:0.2:0.2 After the reaction, pyridine was evaporated, and pure uridine diphosphate acetylated-2-deoxysugar 4 was obtained by silica gel column chromatography (gradient elution with CHCl3:CH3OH:25% NH4OH:H2O system).
 

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