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CAS No. : | 135273-01-7 | MDL No. : | MFCD00237447 |
Formula : | C36H32N2O8S2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | N/A |
M.W : | 684.78 | Pubchem ID : | 14389776 |
Synonyms : |
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TPSA :Topological Polar Surface Area | 202 | H-Bond Acceptor Count : | 10 |
XLogP3 : | 5.8 | H-Bond Donor Count : | 4 |
SP3 : | 0.22 | Rotatable Bond Count : | 15 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With sodium carbonate In 1,4-dioxane; water at 10 - 20℃; for 2.00 h; | Sodium carbonate (4.6 g, 43.6 mmol) and L-cystine (5.0 g, 20.8 mmol) were dissolved in water (200 mL). The resulting solution was cooled to 10° C. FmocCl (11.85 g, 45.8 mmol) was dissolved in dioxane (80 mL), and the resulting solution was added dropwise to the aqueous solution of L-cystine. The solution was stirred for 2 h at 10° C. and allowed to gradually warm to room temperature. A thick white precipitate was obtained that was filtered onto a sintered glass funnel. The product was triturated with diethyl ether (50 mL) and dried in vacuuo for 2 d. N,N'-Bis(Fmoc)-L-cystine (14.0 g, 98percent yield) was obtained as a white powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With sodium carbonate In water; acetone at 50℃; | General procedure: Procedure adapted from that of Agan et al[28]. 407 mg Na2CO3 (3.82 mmol) was dissolved in 30 mL distilled water with stirring. 35 mL acetone was then added followed by 1.91 mmol L-cystine or L-selenocystine. The temperature of the reaction was brought to 50 °C and 1.93g (5.73 mmol) Fmoc-OSu was added in portions over 5 minutes. Heating was removed and the reaction was allowed to progress overnight. At the end of this time, 40 mL 1 HCl was added followed by 50 mL EtOAc. Following vigorous shaking, the layers were separated, and the organic portionwas dried over MgSO4 and concentrated in vacuo to afford the crude bis N-Fmoc dichalcogenide which was purified by recrystallization from CHCl3. |
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