| Identification | More | [Name]
Benzyl glycinate p-toluenesulfonate | [CAS]
1738-76-7 | [Synonyms]
BENZYL GLYCINATE 4-TOLUENESULFONATE SALT
BENZYL GLYCINATE P-TOLUENESULFONATE SALT
GLYCINE BENZYL ESTER 4-TOLUENESULFONATE
GLYCINE BENZYL ESTER 4-TOLUENESULFONATE SALT
GLYCINE BENZYL ESTER 4-TOSYLATE
GLYCINE BENZYL ESTER MONOTOSYLATE
GLYCINE BENZYL ESTER P-TOLUENESULFONATE
GLYCINE BENZYL ESTER P-TOLUENESULFONATE SALT
GLYCINE BENZYL ESTER P-TOSYLATE
GLYCINE BENZYL ESTER PTSA
GLYCINE BENZYL ESTER TOLUENE-4-SULFONATE
GLYCINE BENZYL ESTER TOLUENE-P-SULFONATE
GLYCINE BENZYL ESTER TOSYLATE
GLYCINE-OBZL P-TOSYLATE
GLY-OBZL TOS
GLY-OBZL TSOH
H-GLY-OBZL P-TOSYLATE
H-GLY-OBZL TOS
H-GLY-OBZL TOSOH
L-GLYCINE BENZYL ESTER P-TOLUENESULFONATE SALT | [EINECS(EC#)]
217-094-6 | [Molecular Formula]
C16H19NO5S | [MDL Number]
MFCD00035425 | [Molecular Weight]
337.39 | [MOL File]
1738-76-7.mol |
| Chemical Properties | Back Directory | [Melting point ]
132-134 °C | [storage temp. ]
−20°C
| [solubility ]
methanol: 0.1 g/mL, clear
| [form ]
Solid | [color ]
White to Off-White | [Water Solubility ]
almost transparency | [BRN ]
3600116 | [Major Application]
peptide synthesis | [InChI]
InChI=1S/C9H11NO2.C7H8O3S/c10-6-9(11)12-7-8-4-2-1-3-5-8;1-6-2-4-7(5-3-6)11(8,9)10/h1-5H,6-7,10H2;2-5H,1H3,(H,8,9,10) | [InChIKey]
WJKJXKRHMUXQSL-UHFFFAOYSA-N | [SMILES]
C1(S(O)(=O)=O)=CC=C(C)C=C1.C(OCC1=CC=CC=C1)(=O)CN | [CAS DataBase Reference]
1738-76-7(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
White crystalline | [Uses]
Glycine benzyl ester p-toluenesulfonate salt is a potent crosslinking inhibitor. | [Uses]
Potent crosslinking inhibitors | [Uses]
Racecodotril intermediate | [reaction suitability]
reaction type: solution phase peptide synthesis | [Synthesis]
General procedure: 270 kg of p-toluenesulfonic acid monohydrate and 550 kg of toluene are added to the reactor, stirring is initiated and heating is brought to reflux. The water generated by the reaction was removed by means of a water separator until no water was produced. Subsequently, glycine was added to the reaction vessel. Continue to add 100 kg of reaction solution and 850 kg of benzyl alcohol to the reaction system and maintain reflux. The water generated from the reaction was continuously separated through a water separator until no water was generated, and then the reaction was continued at reflux for 2 hours. Upon completion of the reaction, the reaction solution was cooled to 10°C and stirred for 1 hour. The reaction mixture was filtered and the filter cake was washed with 100 kg of acetone and dried to give 395 kg of glycine benzyl ester p-toluenesulfonate in 88.4% yield and 99.62% purity. | [References]
[1] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 2, p. 519 - 532
[2] Synthesis, 2002, # 8, p. 1017 - 1026
[3] Chemical Communications, 2007, # 36, p. 3711 - 3713
[4] Chemistry - An Asian Journal, 2009, vol. 4, # 2, p. 328 - 335
[5] Journal of Heterocyclic Chemistry, 1994, vol. 31, # 4, p. 707 - 710 |
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