BOC-GLY-OSU Chemical Properties

Melting point:

165-167 °C

Density 

1.31±0.1 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

pka

10.51±0.46(Predicted)

form 

Powder

color 

White

Sensitive 

Hygroscopic

BRN 

1549242

CAS DataBase Reference

3392-07-2(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

F 

3-10-21

MSDS

• Language:English Provider:SigmaAldrich

BOC-GLY-OSU Usage And Synthesis

Chemical Properties

White to off-white powder

Uses

peptide synthesis

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

Step 2: Synthesis of 2,5-dioxopyrrolidin-1-yl 2-(tert-butoxycarbonylamino) acetate. N-Boc-glycine (7.31 g, 41.7 mmol) was dissolved in 100 mL of dichloromethane (DCM) and the solution was cooled to 15 °C. Subsequently, N-hydroxysuccinimide (5.28 g, 45.9 mmol) was added to the cooled solution. Under vigorous stirring, N,N'-dicyclohexylcarbodiimide (9.47 g, 45.9 mmol) was added to the formed suspension. The reaction mixture transformed into a cloudy white suspension within seconds. The reaction mixture was gradually warmed to room temperature and stirring was continued for 1 hour. Upon completion of the reaction, the insoluble by-products were removed by filtration through diatomaceous earth, the filtrate was washed with 50 mL of saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, and finally concentrated under vacuum to give the product as a white crystalline powder. Yield: 7.02 g, yield 61.8%. The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 1.38 (s, 9H), 2.80 (s, 4H), 4.07 (d, J = 6 Hz, 2H), 7.43 (br s, 1H). Mass spectrum (ESI) m/z 567.2 [2M + Na]+.

References

[1] Chemistry - A European Journal, 2016, vol. 22, # 52, p. 18865 - 18872
[2] Journal of the Chemical Society - Perkin Transactions 1, 1998, # 15, p. 2443 - 2449
[3] Chemical communications (Cambridge, England), 2003, # 23, p. 2870 - 2871
[4] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 4, p. 402 - 407
[5] Helvetica Chimica Acta, 2004, vol. 87, # 5, p. 1077 - 1089

BOC-GLY-OSU(3392-07-2)Related Product Information

• BOC-PRO-OSU
• BOC-TRP-OSU
• BOC-ASP(OBZL)-OSU
• BOC-MET-OSU
• BOC-LEU-OSU
• tert-Butoxycarbonyl-L-valine N-hydroxysuccinimide ester
• Succinimido (S)-2-[(tert-butoxycarbonyl)amino]propionate
• BOC-GLY-OSU
• BOC-PHE-OSU
• Glycine
• BOC-Glycine
• BOC-GLU(OBZL)-OSU
• BOC-ILE-OSU
• BOC-GLN-OSU
• BOC-TYR(BZL)-OSU
• BOC-LYS(Z)-OSU
• BOC-SER(BZL)-OSU
• BOC-3,5-DIIODO-TYR-OSU