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O-BENZYL-L-SERINE

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Products Intro: Product Name:O-Benzyl-L-serine
CAS:4726-96-9
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Products Intro: Product Name:O-BENZYL-L-SERINE
CAS:4726-96-9
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  • O-BENZYL-L-SERINE
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  • 2019-07-06
  • CAS:4726-96-9
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  • Purity: 99%
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O-BENZYL-L-SERINE Basic information
Product Name:O-BENZYL-L-SERINE
Synonyms:H-ser(Obzl)-OH;o-(phenylmethyl)-l-serin;O-BENZYL-L-SERINE;SERINE(BZL)-OH;(S)-2-AMINO-3-BENZYLOXYPROPIONIC ACID;O-Benzyl-L-serine >=99.0% (NT);L-Ser(Bzl)-OH;O-Benzyl-L-serine≥ 99% (HPLC)
CAS:4726-96-9
MF:C10H13NO3
MW:195.22
EINECS:225-220-6
Product Categories:Amino Acids and Derivatives;Amino Acid Derivatives;Amino Acid Derivatives;Amino Acids
Mol File:4726-96-9.mol
O-BENZYL-L-SERINE Structure
O-BENZYL-L-SERINE Chemical Properties
Melting point ~227 °C (dec.)
Boiling point 359℃
density 1.217
refractive index 7.3 ° (C=2, 1mol/L HCl)
Fp 171℃
storage temp. Keep in dark place,Inert atmosphere,Room temperature
solubility Aqueous Acid (Slightly), DMSO (Slightly), Methanol (Slightly), Water (Slightly)
form Powder
pka2.10±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 Reference4726-96-9(CAS DataBase Reference)
EPA Substance Registry SystemL-Serine, O-(phenylmethyl)- (4726-96-9)
Safety Information
Safety Statements 24/25
WGK Germany 3
TSCA Yes
HS Code 29225090
MSDS Information
ProviderLanguage
SigmaAldrich English
ALFA English
O-BENZYL-L-SERINE Usage And Synthesis
Chemical PropertiesCrystalline
UsesO-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.
DefinitionChEBI: O-BENZYL-l-SERINE is a L-alpha-amino acid.
reaction suitabilityreaction type: solution phase peptide synthesis
Synthesis
N-BOC-O-Benzyl-L-serine

23680-31-1

O-BENZYL-L-SERINE

4726-96-9

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
Tag:O-BENZYL-L-SERINE(4726-96-9) Related Product Information
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