| Identification | More | [Name]
N-Boc-S-Trityl-L-cysteine | [CAS]
21947-98-8 | [Synonyms]
BOC-CYSTEINE(TRT)-OH
BOC-CYS(TRT)-OH
BOC-L-CYSTEINE(TRITYL)
BOC-L-CYS(TRT)-OH
BOC-L-TRITYL-L-CYSTEINE
BOC-S-TRITYL-L-CYSTEINE
N-ALPHA-BOC-S-TRITYL-L-CYSTEINE
N-ALPHA-T-BOC-S-TRITYL-L-CYSTEINE
N-ALPHA-T-BUTOXYCARBONYL-S-TRITYL-L-CYSTEINE
N-ALPHA-T-BUTYLOXYCARBONYL-S-TRITYL-L-CYSTEINE
N-ALPHA-TERT-BUTYLOXYCARBONYL-S-TRITYL-L-CYSTEINE
N-BOC-S-TRITYL-L-CYSTEINE
N-(TERT-BUTOXYCARBONYL)-S-TRITYL-L-CYSTEINE
(R)-2-TERT-BUTOXYCARBONYLAMINO-3-TRITYLSULFANYL-PROPIONIC ACID
Nα-Boc-S-trityl-L-cysteine
N-T-boc-S-trityl-L-cysteine crystalline
Boc-Cys(Trt)
NALPHA-tert-Butoxycarbonyl-S-trityl-L-cysteine
Nα-Boc-S-trityl-L-cysteine, N-(tert-Butoxycarbonyl)-S-trityl-L-cysteine
Boc-S-Trityl-Cys-OH | [EINECS(EC#)]
244-674-6 | [Molecular Formula]
C27H29NO4S | [MDL Number]
MFCD00038251 | [Molecular Weight]
463.59 | [MOL File]
21947-98-8.mol |
| Chemical Properties | Back Directory | [Appearance]
White to yellow crystalline powder | [Melting point ]
143-146 °C(lit.)
| [alpha ]
27.5 º (c=1, EtOH) | [Boiling point ]
610.9±55.0 °C(Predicted) | [density ]
1.200±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C
| [solubility ]
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | [form ]
Powder | [pka]
3.82±0.10(Predicted) | [color ]
White to off-white | [Optical Rotation]
[α]20/D +27.5°, c = 1 in ethanol | [BRN ]
2028965 | [Major Application]
peptide synthesis | [InChIKey]
JDTOWOURWBDELG-QHCPKHFHSA-N | [SMILES]
C(O)(=O)[C@H](CSC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)NC(OC(C)(C)C)=O | [CAS DataBase Reference]
21947-98-8(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
White to yellow crystalline powder | [Uses]
Boc-Cys(Trt)-OH is used in method for preparing ularitide. | [reaction suitability]
reaction type: Boc solid-phase peptide synthesis | [Synthesis]
General procedure for the synthesis of N-tert-butoxycarbonyl-S-trityl-L-cysteine from di-tert-butyl dicarbonate (Boc2O) and S-trityl-L-cysteine: S-trityl-L-cysteine (5 g, 12.7 mmol) was dissolved in 2N NaOH solution (80 mL), followed by the addition of di-tert-butyl dicarbonate (4.5 g, 20 mmol) . The reaction mixture was stirred at room temperature for 24 hours. After completion of the reaction, the aqueous solution was acidified to pH 2 with concentrated hydrochloric acid and then extracted with dichloromethane (2 x 100 mL). The organic phases were combined, washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the target compound N-tert-butoxycarbonyl-S-trityl-L-cysteine (5.3 g, 90% yield) as a white foamy solid without further purification.1H NMR (DMSO-d6) δ: 1.37 (s, 9H, tert-butyl-CH3); 2.29-2.58 (m , 2H, CH2); 3.76-3.79 (m, 1H, CH); 6.84 (d, J=7.8Hz, 1H, NH); 7.14-7.38 (m, 15H, triphenylmethyl-H).MALDI-TOF MS: m/z 464.8 [M+H]+, molecular weight 463.59 for calculated value C27H29NO4S. | [References]
[1] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 383 - 392
[2] Chemical Communications, 2013, vol. 49, # 92, p. 10808 - 10810
[3] Patent: CN106432014, 2017, A. Location in patent: Paragraph 0096; 0100; 0101; 0102; 0142; 0146; 0147; 0148
[4] Patent: WO2009/137251, 2009, A2. Location in patent: Page/Page column 30; 31
[5] Chemistry of Natural Compounds, 1979, vol. 15, p. 471 - 476 |
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