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)

Flash point:

171℃

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Aqueous Acid (Slightly), DMSO (Slightly), Methanol (Slightly), Water (Slightly)

form 

Powder

pka

2.10±0.10(Predicted)

color 

White to off-white

optical activity

[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)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

TSCA 

Yes

HS Code 

29225090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

O-BENZYL-L-SERINE Usage And Synthesis

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

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

• H-Ser-OtBu · HCl
• O-BENZYL-L-SERINE METHYL ESTER HYDROCHLORIDE
• O-tert-Butyl-L-serine methyl ester hydrochloride
• L-Serine methyl ester hydrochloride
• L-Ser-OBzl.HCl
• H-SER-SER-OH
• L-Serine,O-(triphenylmethyl)-
• H-SER(TBU)-OTBU HCL
• H-SER-ALA-OH
• H-Ser(tBu)-OBzl.HCl
• H-SER(TBU)-OH
• O-ACETYL-L-SERINE
• H-Ser(SO3H)-OH.HCl
• H-Ser(Bzl)-OBzl·HCl
• L-Serinamide hydrochloride
• Boc-Thr(Bzl)-OH
• O-BENZYL-L-SERINE
• Fmoc-THr(Bzl)-OH