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Chemical Structure| 1352173-49-9 Chemical Structure| 1352173-49-9

Structure of 1352173-49-9

Chemical Structure| 1352173-49-9

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Product Details of [ 1352173-49-9 ]

CAS No. :1352173-49-9
Formula : C12H18N2O6
M.W : 286.28
SMILES Code : O(C)[C@H]1[C@@](O[C@H](CO)[C@H]1O)(N2C(OCC)=NC(=O)C=C2)[H]
MDL No. :MFCD27921006
InChI Key :NZNRDRCBHUXJKX-QCNRFFRDSA-N
Pubchem ID :131872654

Safety of [ 1352173-49-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 1352173-49-9 ]

* 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.

  • Downstream synthetic route of [ 1352173-49-9 ]

[ 1352173-49-9 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 64-17-5 ]
  • [ 1352173-41-1 ]
  • [ 1352173-49-9 ]
  • 2
  • [ 1352173-49-9 ]
  • [ 40615-36-9 ]
  • [ 1234923-61-5 ]
  • 4
  • [ 64-17-5 ]
  • [ 1613530-35-0 ]
  • [ 1352173-49-9 ]
YieldReaction ConditionsOperation in experiment
59% With sodium hydrogencarbonate; for 36.0h;Inert atmosphere; Reflux; A mixture of compound 131 (3.36 g, 10 mmol) and sodium bicarbonate (2.1 g, 25 mmol) in ethanol (250 m l_) was refluxed under N2 atmosphere for 36 h. The reaction mixture was cooled to room temperature, and solid sodium bicarbonate was filtered off. The filtrate was concentrated under reduced pressure, and the crude product was purified by flash chromatography on a silica gel column using dichloromethane -methanol (50:1 to 20:1 ) resulting in 1 .7 g of compound 133 in 59% yield. Some starting material was recovered. This product was verified by MS spectrum with good HPLC purity.
59% With sodium hydrogencarbonate; for 36.0h;Inert atmosphere; Compound 133: A mixture of compound 131(3.36 g, 10 mmol) and sodium bicarbonate (2.1 g, 25 mmol) in ethanol (250 mL) was refluxed under N2 atmosphere for 36 h. The reaction mixture was cooled to room temperature, and solid sodium bicarbonate was filtered off. The filtrate wasconcentrated under reduced pressure, and the crude product was purified by flash chromatography on a silica gel column using dichloromethane -methanol (50:1 to 20:1) resulting in 1.7 g of compound 133 in 59% yield. Some starting material was recovered. This product was verified by MS spectrum with good HPLC purity.
59% With sodium hydrogencarbonate; for 36.0h;Inert atmosphere; Reflux; Compound 133: A mixture of compound 131 (3.36 g, 1 0 mmol) and sodium bicarbonate (2.1 25 mmol) in ethanol (250 ml_) was refluxed under N2 atmosphere for 36 h. The reaction mixture s cooled to room temperature, and solid sodium bicarbonate was filtered off. The filtrate was ncentrated under reduced pressure, and the crude product was purified by flash chromatography a silica gel column using dichloromethane -methanol (50:1 to 20: 1 ) resulting in 1 .7 g of compound 3 in 59% yield. Some starting material was recovered. This product was verified by MS spectrum h good H PLC purity.
59% With sodium hydrogencarbonate; for 36.0h;Reflux; Inert atmosphere; Compound 133: A mixture of compound 131 (3.36 g, 10 mmol) and sodium bicarbonate (2.1 g, 25 mmol) in ethanol (250 mL) was refluxed under N2 atmosphere for 36 h. The reaction mixture was cooled to room temperature, and solid sodium bicarbonate was filtered off. The filtrate was concentrated under reduced pressure, and the crude product was purified by flash chromatography on a silica gel column using dichloromethane -methanol (50:1 to 20:1) resulting in 1.7 g of compound 133 in 59% yield. Some starting material was recovered. This product was verified by MS spectrum with good HPLC purity.

  • 5
  • [ 1352173-49-9 ]
  • [ 113886-72-9 ]
YieldReaction ConditionsOperation in experiment
With pyridine; hydrogen sulfide; at -50 - 70℃; for 28.0h;Sealed tube; A solution of compound 133 (1 .7 g, 5.94 mmol) in 500 ml_ of anhydrous pyridine in a high-pressure bump vessel was cooled to -50 C. The in house prepared and dried hydrogen sulfide gas was bubbled in the solution to make it saturated at low temperature. The high-pressure bump was sealed, and heated in an oil bath to 50 C for 4 h, and then increased to 70 C for 24 h. The reaction vessel was cooled to room temperature, and allowed to open to the air slowly. The reaction mixture was concentrated under reduced pressure, and the residue was purified by flash chromatography on a silica gel column providing desired final product 134 with 98.79% HPLC purity (some starting material was recovered). It was characterized by NMR, MS and UV. 1 H NMR (DMSO-ay δ 12.66 (s,1 H), 8.20 (d, 1 H, J = 8.0 Hz) , 6.60 (d, 1 H, J = 3.2 Hz), 6.00 (d, 1 H, J = 8.4 Hz), 5.28 (d, 1 H, J = 4.8 Hz), 5.17 (d, 1 H, J = 6.0 Hz), 4.10 (t, 1 H, J = 5.2 Hz), 3.90 (d, 1 H, J = 3.2 Hz), 3.80 (d, 1 H, J = 4.4 Hz), 3.75 (d, 1 H , J = 4.0 Hz), 3.62 (d, 1 H, J = 4.0 Hz), 3.45 (s, 3H) ; Mass Spectrum : m/z 275 (M + H)+; 297 (M+Na)+.
With pyridine; hydrogen sulfide; at -50 - 70℃; for 28.0h;Sealed tube; 2’-O-Methyl-2-thiouridine (134): A solution of compound 133 (1 .7 g, 5.94 mmol) in 500 mL of anhydrous pyridine in a high-pressure bump vessel was cooled to -50 CC. The in house prepared and dried hydrogen sulfide gas was bubbled in the solution to make it saturated at low temperature. The high-pressure bump was sealed, and heated in an oil bath to 50 C for 4 h, and then increased to 70 CC for 24 h. The reaction vessel was cooled to room temperature, and allowed to open to the airslowly. The reaction mixture was concentrated under reduced pressure, and the residue was purifiedby flash chromatography on a silica gel column providing desired final product 134 with 98.79%HPLC purity (some starting material was recovered). It was characterized by NMR, MS and UV. 1HNMR(DMSO-d5)ö 12.66 (s,1H), 8.20(d, 1H, J= 8.0 Hz), 6.60(d, 1H, J=3.2 Hz), 6.00(d, 1H, J=8.4 Hz), 5.28 (d, 1 H, J= 4.8 Hz), 5.17 (d, 1 H, J= 6.0 Hz), 4.10 (t, 1 H, J= 5.2 Hz), 3.90 (d, 1 H, J= 3.2 Hz), 3.80 (d, 1 H, J= 4.4 Hz), 3.75 (d, 1 H, J= 4.0 Hz), 3.62 (d, 1 H, J= 4.0 Hz), 3.45 (s, 3H); Mass Spectrum: m/z 275 (M + H) 297 (M÷Na).
With pyridine; hydrogen sulfide; at -50 - 70℃; for 28.0h;Sealed tube; 2'-0-Methyl-2-thiouridine (1 34): A solution of compound 133 (1 .7 g, 5.94 mmol) in 500 ml_ of hydrous pyridine in a high-pressure bump vessel was cooled to -50 C. The in house prepared and ed hydrogen sulfide gas was bubbled in the solution to make it saturated at low temperature. The h-pressure bump was sealed, and heated in an oil bath to 50 C for 4 h, and then increased to 70 for 24 h. The reaction vessel was cooled to room temperature, and allowed to open to the air wly. The reaction mixture was concentrated under reduced pressure, and the residue was purified flash chromatography on a silica gel column providing desired final product 134 with 98.79% LC purity (some starting material was recovered) It was characterized by NM R MS and UV 1 H MR (DMS 8.4 Hz), 5.2 z), 3.80 (d, 1 H, J = 4.4 Hz), 3.75 (d, 1 H, J = 4.0 Hz), 3.62 (d, 1 H, J = 4.0 Hz), 3.45 (s, 3H); Mass ectrum: m/z 275 (M + H)+; 297 (M+Na)+.
With pyridine; hydrogen sulfide; at -50 - 70℃; for 28.0h;Sealed tube; 2'-O-Methyl-2-thiouridine (134): A solution of compound 133 (1.7 g, 5.94 mmol) in 500 mL of anhydrous pyridine in a high-pressure bump vessel was cooled to -50 C. The in house prepared and dried hydrogen sulfide gas was bubbled in the solution to make it saturated at low temperature. The high-pressure bump was sealed, and heated in an oil bath to 50 C for 4 h, and then increased to 70 C for 24 h. The reaction vessel was cooled to room temperature, and allowed to open to the air slowly. The reaction mixture was concentrated under reduced pressure, and the residue was purified by flash chromatography on a silica gel column providing desired final product 134 with 98.79% HPLC purity (some starting material was recovered). It was characterized by NMR, MS and UV. 1H NMR (DMSO-d6) δ 12.66 (s,1H), 8.20 (d, 1H, J = 8.0 Hz), 6.60 (d, 1H, J = 3.2 Hz), 6.00 (d, 1H, J = 8.4 Hz), 5.28 (d, 1H, J = 4.8 Hz), 5.17 (d, 1H, J = 6.0 Hz), 4.10 (t, 1H, J = 5.2 Hz), 3.90 (d, 1H, J = 3.2 Hz), 3.80 (d, 1H, J = 4.4 Hz), 3.75 (d, 1H, J = 4.0 Hz), 3.62 (d, 1H, J = 4.0 Hz), 3.45 (s, 3H); Mass Spectrum: m/z 275 (M + H)+; 297 (M+Na)+.

 

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