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| | (2R,3S,4R,5R)-2-(hydroxyMethyl)-5-(6-((2-(Methylthio)ethyl)aMino)-2-((3,3,3-trifluoropropyl)thio)-9H-purin-9-yl)tetrahydrofuran-3,4-diol Basic information |
| Product Name: | (2R,3S,4R,5R)-2-(hydroxyMethyl)-5-(6-((2-(Methylthio)ethyl)aMino)-2-((3,3,3-trifluoropropyl)thio)-9H-purin-9-yl)tetrahydrofuran-3,4-diol | | Synonyms: | (2R,3S,4R,5R)-2-(hydroxyMethyl)-5-(6-((2-(Methylthio)ethyl)aMino)-2-((3,3,3-trifluoropropyl)thio)-9H-purin-9-yl)tetrahydrofuran-3,4-diol;(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-((2-(methylthio)ethyl)amino)-2- ((3,3,3-trifluoropropyl)thio)-9H-purin-9-yl)tetrahydrofuran-3,4-diol N6-(2-Methylthioethyl)-2-(3,3,3-trifluoropropylthio)adenosine;((3aR,4R,6R,6aR)-6-(6-amino-2-((3,3,3-trifluoropropyl)thio)-9H- purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol;N-[2-(Methylthio)ethyl]-2-[(3,3,3-trifluoropropyl)thio]adenosine;Adenosine, N-[2-(Methylthio)ethyl]-2-[(3,3,3-trifluoropropyl)thio]- (9CI);N6-(2-Methylthioethyl)-2-(3,3,3-trifluoropropylthio)adenosine;Cangrelor Intermediate;(2R,3S,4R,5R)-2-(hydroxyMethyl)-5-(6-((2-(Methylthio)ethyl)aMino)-2-((3,3,3-trifluoropropyl)thio)-9H-purin-9-yl) | | CAS: | 163706-58-9 | | MF: | C16H22F3N5O4S2 | | MW: | 469.5 | | EINECS: | 812-944-8 | | Product Categories: | | | Mol File: | 163706-58-9.mol |  |
| | (2R,3S,4R,5R)-2-(hydroxyMethyl)-5-(6-((2-(Methylthio)ethyl)aMino)-2-((3,3,3-trifluoropropyl)thio)-9H-purin-9-yl)tetrahydrofuran-3,4-diol Chemical Properties |
| Melting point | 179-181°C | | Boiling point | 747.5±70.0 °C(Predicted) | | density | 1.70±0.1 g/cm3(Predicted) | | storage temp. | 2-8°C(protect from light) | | solubility | Chloroform (Slightly), Methanol (Slightly) | | pka | 13.08±0.70(Predicted) | | form | Solid | | color | White to Light Yellow | | InChIKey | ZGVUPMJCZYBIDI-IDTAVKCVSA-N | | SMILES | OC[C@H]1O[C@@H](N2C3C(=C(N=C(SCCC(F)(F)F)N=3)NCCSC)N=C2)[C@H](O)[C@@H]1O |
| | (2R,3S,4R,5R)-2-(hydroxyMethyl)-5-(6-((2-(Methylthio)ethyl)aMino)-2-((3,3,3-trifluoropropyl)thio)-9H-purin-9-yl)tetrahydrofuran-3,4-diol Usage And Synthesis |
| Uses | N-[2-(Methylthio)ethyl]-2-[(3,3,3-trifluoropropyl)thio]-adenosine is used for developing platelet P2T receptor antagonists, which have potential applications for antithrombotic therapy. | | Synthesis | The general procedure for the synthesis of (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-((2-(methylthio)ethyl)amino)-2-((3,3,3-trifluoropropyl)thio)-9H-purin-9-yl)tetrahydrofuran-3,4-diol, using the compound (CAS:163706-57-8) as a raw material, is as follows: the crude obtained in Example 38 was reacted with the crude product (60.3 g) was co-dissolved with potassium carbonate (199 g, 1.44 mol) in 600 mL of isopropanol, heated to reflux and the reaction was maintained for 2 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure to give a concentrate. To the concentrate, 300 mL of water was added and the pH was adjusted to about 7 using acetic acid with continuous stirring for 0.5 hours. Subsequently, the reaction mixture was filtered and the solid product was collected and dried to give a final 33.8 g of pale yellow solid product. The overall yield of this three-step synthetic process was 75% (based on the compound of formula (10)) and the product purity was 97.9% as analyzed by high performance liquid chromatography (HPLC). | | References | [1] Patent: CN107973798, 2018, A. Location in patent: Paragraph 0259; 0264; 0265-0267; 0270; 0273
[2] Journal of Medicinal Chemistry, 1999, vol. 42, # 2, p. 213 - 220
[3] Patent: CN107973832, 2018, A. Location in patent: Paragraph 0028; 0253-0270 |
| | (2R,3S,4R,5R)-2-(hydroxyMethyl)-5-(6-((2-(Methylthio)ethyl)aMino)-2-((3,3,3-trifluoropropyl)thio)-9H-purin-9-yl)tetrahydrofuran-3,4-diol Preparation Products And Raw materials |
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