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[ CAS No. 1256490-31-9 ] {[proInfo.proName]}

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Chemical Structure| 1256490-31-9
Chemical Structure| 1256490-31-9
Structure of 1256490-31-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1256490-31-9 ]

CAS No. :1256490-31-9 MDL No. :MFCD28978357
Formula : C18H21N2O7P Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 408.34 Pubchem ID :-
Synonyms :

Safety of [ 1256490-31-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1256490-31-9 ]

* 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 [ 1256490-31-9 ]

[ 1256490-31-9 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 777-52-6 ]
  • [ 39613-92-8 ]
  • [ 1256490-49-9 ]
  • [ 1256490-31-9 ]
YieldReaction ConditionsOperation in experiment
To a stirred solution of 4-nitrophenyl phoshorodichloridate 12.8g, 50 mmol) in dichloromethane (100 mL) was added a solution of phenol and triethylamine (7.7 niL, 55 mmol) in dichloromethane (100 mL) at -780C over a period of 20min. The mixture was stirred at this temperature for 30min and then transferred to another round bottom flask containing L-alanine isopropyl ester hydrochloride (8.38g, 50mmol) in dichloromethane (100 mL) at 0C. To the mixture was added second portion of triethylamine (14.6 mL, 105 mmol) over a period of 15min.The mixture was stirred at 0C for Ih and then the solvent was evaporated. The residue was triturated with ethyl acetate (150 mL) and the white solid was filtered off. The filtrate was concentrated under reduced pressure to give pale yellow oil. The crude compound was chromatographed using 0-20% ethyl acetate/hexanes gradient to give product (17g, 83 %yield) as a mixture of diastereomers in about 1:1 ratio. 31P NMR (162 MHz, DMSO-d6): delta -0.31, -0.47; 1H NMR (400 MHz, DMSO-d6): delta 8.31-8.27 (m, 2H), 7.51-7.37(m, 4H), 7.27-7.19(m, 3H), 6.70-6.63(m, IH), 4.85-4.78(m, IH), 3.97- 3.86(m, IH), 1.21-1.19(m, 3H), 1.11-1.09 (m, 6H); MS (ESI) m/z 407 (M-I)+. 31P NMR (162 MHz, CDCl3): delta -2.05, -2.10; 1H NMR (400 MHz, CDCl3): delta 8.22 (d, J = 9.2Hz, 2H), 7.41-7.33(m, 4H), 7.26-7.18(m, 3H), 5.05-4.96(m, IH), 4.14-4.05(m, IH), 3.93-3.88(m, IH), 1.38(d, J = 6.8Hz, 3H), 1.22 (dd, J = 6.2 3.0Hz, 6H); MS (ESI) m/z 407 (M-I)+.
  • 2
  • [ 863329-66-2 ]
  • [ 1256490-49-9 ]
  • [ 1256490-31-9 ]
  • [ 1190307-88-0 ]
  • [ 1190308-01-0 ]
YieldReaction ConditionsOperation in experiment
To a stirred solution of l-((2R,3R,4R,5R)-3-Fluoro-4-hydroxy-5- hydroxymethyl-3-methyl-tetrahydro-furan-2-yl)- 1 H-pyrimidine-2,4-dione (130mg, 0.5mmol) in dry THF (1.5mL) was added a 1.0M solution of tert-butylmagnesium chloride (1.05mL, 1.05mmol, 2.1 equiv)) at room temperature over a period of 5min. After 30min, a solution of (S)-2-[(4-nitro-phenoxy)-phenoxy-phosphorylamino] propionic acid isopropyl ester (1:1 mixture of isomers, 408mg, lmmol) in THF (1.5mL) was added drop-wise over a period of 5min. The mixture was allowed to stir at room temperature for 48h and then quenched with saturated aqueous NH4Cl (2OmL). The mixture was partitioned between ethyl acetate (5OmL) and water (2OmL). The combined organic extract was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give a pale yellow residue. Column chromatography of the residue using 0-2% MeOH/dichloromethane gradient gave a white foamy solid (125mg, 47% yield, mixture of Sp-4/Rp-4 in about 3.05:1.0 ratio
  • 3
  • [ 863329-66-2 ]
  • [ 1256490-31-9 ]
  • [ 1190307-88-0 ]
YieldReaction ConditionsOperation in experiment
67.6% At room temperature,Add (2'R)-2'-deoxy-2'-fluoro-2'-methyluridine (1.30G, 5mol) and anhydrous tetrahydrofuran (30 ml) to the reaction flask, stir and dissolve, and add tert-butylmagnesium chloride dropwise. (2.28 g, 24 mol) in tetrahydrofuran (5 ml). After the dropwise addition, the reaction was stirred for 1 hour. Continue dropping of isopropyl (2S)-2-(((4-ylphenoxy)phenoxyphosphoryl)amino)propionate(4.90 g, 12 mol) in tetrahydrofuran (20 ml). After stirring for 48 hours at room temperature, the reaction was complete by TLC. The reaction solution was poured into 10 ml of saturated ammonium chloride solution and extracted three times with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and the resulting oil was distilled under reduced pressure by silica gel column chromatography (dichloromethane/methanol= 10/1) and recrystallization from methyl tert-butyl ether/n-pentane gave 1.76 g of sofosbuvir as a white solid with a yield of 67.6%
Compound (S)-8To a dry, argon purged round-bottom flask were added compound 7 (prepared according to J. Med. Chem., 2005, 48, 5504-5508, 100 mg, 0.38 mmol), anhydrous THF (3 mL) and anhydrous NMP (1 mL). The slurry was stirred for 10 min. and the flask was place in a water bath at room temperature. i-Butylmagnesium chloride in THF (1.0 M, 0.76 mL) was dropwise added, and the mixture was stirred for an additional 10 min. A solution of (S)-C (313 mg, 0.76 mmol) in THF (2 mL) was then added. The flask was place in a heating oil bath pre-set at 55 C and the mixture was stirred until compound 7 was almost consumed. After ~2.5 h, the reaction mixture was cooled to room temperature, and methanol (1 mL) was added. Solvents were removed under reduced pressure and the residue was purified by RP-HPLC followed by silica gel column chromatography, affording (S)-8 (130 mg, 65%). 1H NMR (400 MHz, CDC13): 5 8.51 (brs, IH), 7.46 (d, IH), 7.2-7.4 (m, 5H), 6.28 (d, IH), 5.70 (dd, IH), 5.01 (m, IH), 4.49 (m, 2H), 3.8-4.1 (m, 4H), 1.41 (d, 3H), 1.35 (d, 3H), 1.24 (d, 6H). 31P NMR (162.1 MHz, CDC13): 5 3.70 (s). MS = 530.0 (M + H+), 528.0 (M - H+). Chiral HPLC retention time (Chiralpak AS-H, 250 x 4.6 mm 5 micron, 100% CH3CN, 1 mL/min flow rate); 6.5 min vs. 5.2 min for the R-isomer). Using the general procedures described for the preparation of Compound (S)- C or Compound (R)-C, Compounds 10-24 ma be re are .
  • 4
  • [ 777-52-6 ]
  • [ 39825-33-7 ]
  • [ 108-95-2 ]
  • [ 1256490-49-9 ]
  • [ 1256490-31-9 ]
YieldReaction ConditionsOperation in experiment
To a stirred solution of 4-nitrophenyldichlorophosphate (5 g, 19.8 mmol) in dry DCM (40 ml) was added a solution of phenol (1 .86 g, 19.8 mmol) and triethylamine (3 mL, 21 .8 mmol) in dry DCM (50 mL) at -78 C over a period of 30 min. The mixture was stirred at this temperature for 60 min, then transferred to another flask containing a solution of compound (S)-isopropyl 2- aminopropanoate (3.3 g, 19.8 mmol) in dry DCM (40 ml_) at -5 C over a period of 15 min. To this mixture was added a second portion of TEA (6 ml_, 43.3 mmol) at -5 C over a period of 20 min. The mixture was stirred at 0 C for 3h, then the solvent was removed under reduced pressure. The residue was taken in EtOAc (200 mL) and washed with water (50 mL), dried over Na2S04 and the solvents were removed under reduced pressure to give the crude product as an oil, which was purified by column chromatography using 0-20% EtOAc/Hexane gradient and 230-400 mesh silica gel to give a mixture of diastereomers in about 1 :1 ratio. The two diastereomers were separated by SFC which gave the title compound, Isomer 1 (1 .5 g, 20%) and Isomer 2 (1 .5 g, 18%) as solids.
  • 5
  • [ 1256490-31-9 ]
  • [ 1191237-69-0 ]
  • (S)-isopropyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f ][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate [ No CAS ]
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