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| | (S)-4-ISOPROPYLTHIAZOLIDINE-2-THIONE Basic information |
| | (S)-4-ISOPROPYLTHIAZOLIDINE-2-THIONE Chemical Properties |
| Melting point | 69-71 °C | | Boiling point | 223.3±23.0 °C(Predicted) | | density | 1.17±0.1 g/cm3(Predicted) | | storage temp. | Keep in dark place,Inert atmosphere,Room temperature | | solubility | almost transparency in Chloroform | | pka | 12.95±0.40(Predicted) | | form | powder to crystal | | color | White to Almost white | | Optical Rotation | [α]20/D -37±3°, c = 1 in chloroform | | InChI | 1S/C6H11NS2/c1-4(2)5-3-9-6(8)7-5/h4-5H,3H2,1-2H3,(H,7,8)/t5-/m1/s1 | | InChIKey | CWIZUGZKLJDJLE-RXMQYKEDSA-N | | SMILES | CC(C)[C@H]1CSC(=S)N1 | | CAS DataBase Reference | 76186-04-4(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36/37/39 | | WGK Germany | 3 | | Hazard Note | Irritant | | HS Code | 2934100090 | | Storage Class | 11 - Combustible Solids |
| | (S)-4-ISOPROPYLTHIAZOLIDINE-2-THIONE Usage And Synthesis |
| Uses | (S)-4-Isopropylthiazolidine-2-thione may be used as a chiral auxiliary for the stereochemical induction at the phosphorus atom during the diastereoselective synthesis of aryloxy phosphoramidate prodrugs of 3μ-deoxy-2μ,3μ-didehydrothymidine monophosphate (d4TMP).', 'A highly selective and efficient chiral auxiliary which can be directly reduced to its corresponding aldehyde and the chiral auxiliary by reductive cleavage with diisobutylaluminum hydride. | | Synthesis | The yields of the following procedures are higher than those reported in the literature (Erik Galvez, P. R., Felix Urp. (2009). Organic Synthesis, 86, 70). To a sealed tube was added aqueous KOH (2.7 g, 48.4 mmol, 5 eq., dissolved in 8 mL of water), 2 mL of ethanol, CS2 (2.9 mL, 48.4 mmol, 5 eq.) and (S)-(+)-2-amino-3-methyl-1-butanol (1.0 g, 9.69 mmol, 1 eq.). The reaction mixture was heated at 80 °C for 15 h, followed by purging with N2 to remove excess CS2. The reaction solution was neutralized with 1 M aqueous HCl and extracted with EtOAc (3 x 60 mL). The organic layers were combined, washed with brine (5 mL), dried over MgSO4 and concentrated in vacuum. The crude product was purified by silica gel column chromatography to afford (S)-4-isopropylthiazolidine-2-thione as a yellow solid (1.19 g, 76% yield). The characterization data of the product were in agreement with literature reports. | | References | [1] European Journal of Organic Chemistry, 2011, # 23, p. 4397 - 4408
[2] Organic Syntheses, 2009, vol. 86, p. 70 - 80
[3] Tetrahedron, 2008, vol. 64, # 24, p. 5637 - 5644
[4] Organic Letters, 2011, vol. 13, # 21, p. 5916 - 5919
[5] European Journal of Organic Chemistry, 2009, # 33, p. 5841 - 5846 |
| | (S)-4-ISOPROPYLTHIAZOLIDINE-2-THIONE Preparation Products And Raw materials |
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