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Chemical Structure| 874638-93-4 Chemical Structure| 874638-93-4

Structure of 874638-93-4

Chemical Structure| 874638-93-4

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Product Details of [ 874638-93-4 ]

CAS No. :874638-93-4
Formula : C22H21FO7
M.W : 416.40
SMILES Code : O=C(O[C@@H]1[C@@H](COC(C2=CC=CC=C2)=O)OC(OC(C)=O)[C@@]1(F)C)C3=CC=CC=C3

Safety of [ 874638-93-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Application In Synthesis of [ 874638-93-4 ]

* 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 [ 874638-93-4 ]

[ 874638-93-4 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 874638-93-4 ]
  • [ 10357-07-0 ]
  • (2R,3R,4R,5R)-5-(4-benzamido-5-fluoro-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
9.6% In a 50 mL pear-shaped flask charged with N-(5-fluoro-2-oxo-l,2-dihydropyrimidin-4- yl)benzamide (0.185 g, 0.793 mmol) was added bis(trimethylsilyl)amine (1.77 ml, 8.45 mmol) and ammonium sulfate (2.6 mg, 0.02 mmol) under N2. This was heated for refluxing for 2 h, after cooling to rt, solvent was removed in vacuo and further dried under high vacuum for 1 h. The residue was dissolved in dry chlorobenzene (10 ml) and (2R,3R,4R,5R)-5-acetoxy-2- ((benzoyloxy)methyl)-4-fluoro-4-methyl-tetrahydrofuran-3-yl benzoate (0.22 g, 0.53 mmol) was added. Then SnCl4 (0.27 ml, 2.3 mmol) was added dropwise. After stirring at rt for 1 h, this was heated to 60 C overnight. After cooling to 0 C, solid sodium bicarbonate (0.85 g) was added, followed by EtOAc (5 mL). This was allowed to stir for 15 min and then water (0.5 mL) was added slowly. The insoluble material was filtered off and washed wtih more EtOAc (2.5 mL). The filtrate was washed with water once, bine once, dried (Na2S04) and concentrated in vacuo. The crude material was purified by Si02 column chromatography eluting from 10% to 35% EtOAc in hexanes to afford (2R,3R,4R,5R)-5-(4-benzamido-5-fluoro-2-oxopyrimidin-l(2H)-yl)- 2-((benzoyloxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate (30 mg, 9.6 % yield) as a white solid. 1H NMR (400 MHz, CDC13) delta 8.29 (d, J = 7.2 Hz 1H), 8.14 - 8.09 (m, 4H), 7.83 (d, J = 5.6 Hz, 1H), 7.65 - 7.47 (m, 10H), 6.36 (d, J = 21.2 Hz, 1H), 5.51 (dd, J = 22.0, 9.6 Hz, 1H), 4.86 - 4.64 (m, 3H), 1.52 (d, J= 22.0 Hz, 3H). LCMS C3iH26F2N307 [M+H+]; calculated: 589.2, found 590.1.
 

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