| Identification | More | [Name]
O-BENZYL-L-SERINE | [CAS]
4726-96-9 | [Synonyms]
BENZYL-L-SERINE
H-L-SER(BZL)-OH
H-SER(BZL)-OH
L-SERINE BENZYL ETHER
O-BENZYL-L-SERINE
(S)-2-AMINO-3-BENZYLOXYPROPIONIC ACID
SERINE(BZL)-OH
o-(phenylmethyl)-l-serin
O-BENZYL-L-SERINE CRYSTALLINE
O-Benzyl-L-serine,99%
O-Benzyl-L-serine, (S)-2-Amino-3-benzyloxypropanoic acid
(S)-2-Amino-3-(benzyloxy)propanoic acid
3-(Benzyloxy)alanine
3-(Benzyloxy)-L-alanine
O-(Phenylmethyl)-L-serine | [EINECS(EC#)]
225-220-6 | [Molecular Formula]
C10H13NO3 | [MDL Number]
MFCD00065937 | [Molecular Weight]
195.22 | [MOL File]
4726-96-9.mol |
| Chemical Properties | Back Directory | [Appearance]
Crystalline | [Melting point ]
~227 °C (dec.) | [Boiling point ]
359℃ | [density ]
1.217 | [refractive index ]
7.3 ° (C=2, 1mol/L HCl) | [Fp ]
171℃ | [storage temp. ]
Store at RT. | [solubility ]
Aqueous Acid (Slightly), DMSO (Slightly), Methanol (Slightly), Water (Slightly) | [form ]
Powder | [pka]
2.10±0.10(Predicted) | [color ]
White to off-white | [Optical Rotation]
[α]20/D +21±2°, c = 2% in acetic acid: water (4:1) (+ 1 Eq HCl) | [BRN ]
2114846 | [CAS DataBase Reference]
4726-96-9(CAS DataBase Reference) | [EPA Substance Registry System]
L-Serine, O-(phenylmethyl)- (4726-96-9) |
| Hazard Information | Back Directory | [Chemical Properties]
Crystalline | [Uses]
O-Benzyl-L-Serine is used in the preparation of serine analogs as specific agonists for NMDA receptor glycine binding sites. It also functions as an eluent for ligand exchange chromatography for the separation of constrained glutamate receptor ligands. | [Definition]
ChEBI: O-BENZYL-l-SERINE is a L-alpha-amino acid. | [reaction suitability]
reaction type: solution phase peptide synthesis | [Synthesis]
The general procedure for the synthesis of (S)-2-amino-3-(benzyloxy)propionic acid from N-BOC-O-benzyl-L-serine was as follows: the compound obtained in the previous step was dissolved in an appropriate amount of dry dichloromethane (DCM), 1.0 mL of trifluoroacetic acid (TFA) and 0.1 mL of triethylsilane were added, and the reaction was stirred for 2 hr at room temperature, and the reaction was monitored by thin-layer chromatography (TLC) The reaction was monitored until complete. Upon completion of the reaction, the pH of the reaction solution was adjusted to 7?8 with saturated sodium bicarbonate solution and subsequently diluted with the addition of dichloromethane (DCM). The organic phase was washed twice with saturated brine and then concentrated to give a yellow oily liquid. Finally, the product was purified by silica gel column chromatography (eluent ratio of chloroform:methanol=15:1) to give a yellow powdery solid product in 62.3% yield. | [References]
[1] Patent: CN107082754, 2017, A. Location in patent: Paragraph 0119; 0124
[2] Organic Process Research and Development, 2003, vol. 7, # 4, p. 521 - 532
[3] Tetrahedron Letters, 2014, vol. 55, # 30, p. 4149 - 4151
[4] ACS Chemical Neuroscience, 2017, vol. 8, # 8, p. 1681 - 1687
[5] Patent: WO2017/189866, 2017, A1. Location in patent: Paragraph 0210 |
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