Boc-S-trityl-D-cysteine Chemical Properties

Melting point:

146-149°C

Boiling point:

610.9±55.0 °C(Predicted)

Density 

1.200±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,2-8°C

solubility 

Chloroform (Slightly), DMSO (Slightly), Ethanol (Sparingly)

form 

Solid

pka

3.82±0.10(Predicted)

color 

White to Off-White

CAS DataBase Reference

87494-13-1

Boc-S-trityl-D-cysteine Usage And Synthesis

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 and S-trityl-L-cysteine: to a solution of 2N NaOH (80 mL) of S-trityl-L-cysteine (5 g, 12.7 mmol) was added di-tert-butyl dicarbonate (4.5 g, 20 mmol), and the reaction mixture was at room temperature The reaction mixture was stirred for 24 hours at room temperature. Upon completion of the reaction, the aqueous solution was acidified to pH 2 with concentrated HCl and then extracted with CH2Cl2 (2 x 100 mL). The organic phases were combined, washed with brine, dried and concentrated under reduced pressure to give N-Boc-S-trityl-L-cysteine (5.3 g, 90%) as a white foam, which did not need to be further purified.1H NMR (DMSO): δ (ppm) 1.37 (s, 9H, 3 × CH3); 2.29-2.58 (m, 2H, CH2); 3.76- 3.79 (m, 1H, CH); 6.84 (d, J = 7.8 Hz, 1H, NH); 7.14-7.38 (m, 15H, triphenylmethyl-H).MALDI-TOF MS: m/z 464.8 Da [M + H], C27H29NO4S, molecular weight: 463.59.

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

Boc-S-trityl-D-cysteine(87494-13-1)Related Product Information

• N-(tert-Butoxycarbonyl)-L-alanine
• FMOC-D-alanine
• Nalpha-Fmoc-Ndelta-trityl-L-glutamine
• Fmoc-Asn(Trt)-OH
• FMOC-CYS(MMT)-OH
• FMOC-S-trityl-L-cysteine
• Fmoc-S-acetamidomethyl-L-cysteine
• BOC-D-Alanine
• Boc-beta-cyclohexyl-D-alanine monohydrate
• Boc-D-aspartic acid 4-benzyl ester
• BOC-D-Cysteine (Boc-D-Cys-OH )
• Boc-D-aspartic acid 4-cyslohexyl ester
• BOC-D-ASP(OTBU)-OH DCHA
• Boc-alpha-Cyclohexyl-D-glycine
• BOC-D-ASP(OBZL)-OH
• N-Boc-S-Trityl-L-cysteine