2-((3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)ethanol L-tat
Introduction：Basic information about 2-((3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)ethanol L-tat, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
2-((3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)ethanol L-tataric acid Basic information
| Product Name: | 2-((3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)ethanol L-tataric acid |
| Synonyms: | 2-((3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)ethanol L-tataric acid;2-[[(3aR,4S,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-ethanol (2R,3R)-2,3-dihydroxybutanedioate;Ticagrelor InterMediate 2;2-((3aR,4R,6R,6aR)-6-Amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)ethanol L-tataric acid;2-[[(3aR, 4S, 6R, 6aS)6-aMinotetrahydro-2,2-diMethyl-4-H-cyclopenta-1,3-dioxol-4-yl]oxy]-(2R,3R)-2,3-dihydroxybutanedioate ethanol;2-((3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)ethanol L-tat;2-(((3aR,4S,6R,6aS)-6-Amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)ethanol (2R,3R,4S,5R)-2,3,4,5-tetrahydroxyhexanedioate;2-[[3aR,4s,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol-L-tartrate |
| CAS: | 376608-65-0 |
| MF: | C14H25NO10 |
| MW: | 367.35 |
| EINECS: | 1308068-626-2 |
| Product Categories: | Intermediate of Ticagrelor;376608-65-0 |
| Mol File: | 376608-65-0.mol |
2-((3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)ethanol L-tataric acid Chemical Properties
| storage temp. | Keep in dark place,Sealed in dry,Room Temperature |
| InChI | InChI=1/C10H19NO4.C4H6O6/c1-10(2)14-8-6(11)5-7(9(8)15-10)13-4-3-12;5-1(3(7)8)2(6)4(9)10/h6-9,12H,3-5,11H2,1-2H3;1-2,5-6H,(H,7,8)(H,9,10)/t6-,7+,8+,9-;1-,2-/s3 |
| InChIKey | XEYNXCGNMKWIDO-PLHQUINWNA-N |
| SMILES | [C@H](O)(C(=O)O)[C@@H](O)C(=O)O.O([C@H]1C[C@@H](N)[C@]2([H])OC(C)(C)O[C@]12[H])CCO |&1:0,5,11,13,15,22,r| |
Safety Information
| Safety Statements | 24/25 |
| HS Code | 29329990 |
| Chemical Properties | White to off-white powder |
| Uses | 2-[[(3aR,4S,6R,6aS)-6-aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-Ethanol (2R,3R)-2,3-dihydroxybutanedioate is a useful building block, most frequently used in the preparation of the antithrombotic agent Ticagrelor. |
| Synthesis | Put 50g of benzyl ((3aS,4R,6S,6aR)-6-(2-hydroxyethoxy)-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-yl)carbamate and 250 mL of methanol into a 1L four-necked flask 1.Add 10 g of 10% palladium carbon and 22.4 g of ammonium formate to bottle 1 at 20-30°C. After the addition, the temperature is raised to 40-50°C, and the reaction is stirred for 10 hours and filtered with suction. The filtrate was transferred to a 1L four-neck flask 2, and the temperature was raised to 40-50°C again. 21.4g L-tartaric acid was added to batches 2 while stirring. Then, continue to stir the reaction for 1 hour, slowly lower the temperature to 10-20°C, and stir the reaction for 2 hours, and a large number of white solids can be seen to precipitate. Continue to lower the temperature to 0-10°C and react for 0.5h, then suction filter and wash the filter cake once with 50mL ethanol. The filter cake was dried under reduced pressure at 40° C. for 4 hours to obtain 45.7 g of white powdery solid 2-((3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)ethanol L-tataric acid with a yield of 87.47%. |
| Application | 2-((3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)ethanol L-tataric acid could be used to synthesis 2-[((3aR,4S,6R,6aS)-6-{[5-nitro-6-chloro-2-(propylthio)- 4-pyrimidinyl]amino}-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxoI-4-yl)oxy]-1-ethanol. |
| References | [1] Patent: CN106279095, 2017, A. Location in patent: Paragraph 0050 |
2-((3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)ethanol L-tataric acid Preparation Products And Raw materials
| Raw materials | N-[(3aS,4R,6S,6aR)-Tetrahydro-6-(2-hydroxyethoxy)-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]carbamic acid phenylmethyl ester-->1-Acetyladamantane Intermediate-->L(+)-Tartaric acid-->L(+)-Tartaric acid |
