4726-96-9

Basic information

• Product Name: O-BENZYL-L-SERINE
• Synonyms: H-ser(Obzl)-OH;O-Benzyl-L-serine >=99.0% (NT);L-Ser(Bzl)-OH;O-Benzyl-L-serine≥ 99% (HPLC);o-(phenylmethyl)-l-serin;O-BENZYL-L-SERINE;SERINE(BZL)-OH;(S)-2-AMINO-3-BENZYLOXYPROPIONIC ACID
• CAS NO: 4726-96-9
• Molecular Formula: C₁₀H₁₃NO₃
• Molecular Weight: 195.22
• EINECS: 225-220-6
• Product Categories: Amino Acid Derivatives;Amino Acids;Amino Acids and Derivatives;Amino Acid Derivatives
• Mol File: 4726-96-9.mol
• Article Data: 14

Chemical Properties

• Melting Point: ~227 °C (dec.)
• Boiling Point: 359℃
• Flash Point: 171℃
• Appearance: White to off-white/Powder
• Density: 1.217
• Vapor Pressure: 8.83E-06mmHg at 25°C
• Refractive Index: 7.3 ° (C=2, 1mol/L HCl)
• Storage Temp.: Store at RT.
• Solubility: Aqueous Acid (Slightly), DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• PKA: 2.10±0.10(Predicted)
• BRN: 2114846
• CAS DataBase Reference: O-BENZYL-L-SERINE(CAS DataBase Reference)
• NIST Chemistry Reference: O-BENZYL-L-SERINE(4726-96-9)
• EPA Substance Registry System: O-BENZYL-L-SERINE(4726-96-9)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 4726-96-9(Hazardous Substances Data)

Usage

Description

O-Benzyl-L-Serine is a crystalline organic compound that is widely utilized in the synthesis of serine analogs and serves as an essential component in various applications across different industries. It is known for its unique chemical properties that make it a valuable asset in the field of chemistry and pharmaceuticals.

Uses

Used in Pharmaceutical Industry:
O-Benzyl-L-Serine is used as a key intermediate in the preparation of serine analogs, which act as specific agonists for N-methyl-D-aspartate (NMDA) receptor glycine binding sites. These agonists play a crucial role in modulating the activity of the NMDA receptor, which is involved in various neurological processes, including learning, memory, and synaptic plasticity. O-BENZYL-L-SERINE's ability to interact with these receptors makes it a promising candidate for the development of therapeutic agents targeting neurological disorders.
Used in Chemical and Analytical Industry:
O-Benzyl-L-Serine also functions as an eluent in ligand exchange chromatography, a technique used for the separation of constrained glutamate receptor ligands. This application is particularly relevant in the field of drug discovery and development, as it aids in the isolation and purification of specific compounds with potential therapeutic properties. O-BENZYL-L-SERINE's effectiveness as an eluent is attributed to its unique chemical properties, which enable it to selectively interact with target molecules and facilitate their separation from complex mixtures.

InChI:InChI=1/C10H13NO3/c11-9(10(12)13)7-14-6-8-4-2-1-3-5-8/h1-5,9H,6-7,11H2,(H,12,13)/t9-/m0/s1

Upstream product

• 35436-77-2 N-acetyl-O-benzyl-DL-serine 
• 20806-43-3 Z-Ser(Bzl)-OH 
• 4218-63-7 N-(4-Methoxybenzyloxycarbonyl)-O-benzyl-L-serine 
• 5513-74-6 O-Benzil-N-formil-(S)-(+)-serina 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 5445-44-3 O-benzylserine 
• 20409-07-8 N-Formyl-O-benzyl-DL-serin 
• 23680-31-1 BOC-O-benzyl-L-serine 

Downstream Products

• 46460-82-6 O-benzyl-L-serine methyl ester 
• 20806-43-3 Z-Ser(Bzl)-OH 
• 1581-95-9 O-benzyl-N-trifluoroacetyl-L-serine 
• 5513-74-6 O-Benzil-N-formil-(S)-(+)-serina 
• 58577-87-0 O-benzyl-L-serinol 
• 62061-51-2 (Z)-3-Benzyloxyacrylsaeure 
• 62076-21-5 (S)-2-bromo-3-(phenylmethoxy)propanoic acid 
• 3062-02-0 O-Benzyl-N-chloracetyl-L-serin 
• 19525-87-2 O-methyl O-benzyl-L-serinate hydrochloride 
• 120105-77-3 [2-Benzyloxy-eth-(E)-ylidene]-(6-methoxy-1,4-dimethyl-9H-carbazol-3-ylmethyl)-amine 
• 102249-13-8 N^α,N^G,N^G-tribenzyloxycarbonylarginyl-(O-benzyl)serine 
• 23680-31-1 BOC-O-benzyl-L-serine 
• 127488-83-9 Ser(OBzl)-tetra-n-butyl-ammonium salt 
• 96935-92-1 Z(OMe)-Ser(Bzl)-Ser(Bzl)-OH*DCHA 

Relevant articles and documents

Cinnamic acid derivative with aldose reductase inhibitory activity as well as preparation method and application thereof

The invention discloses a cinnamic acid derivative with aldose reductase inhibitory activity, a preparation method thereof and an application of the cinnamic acid derivative in preparation of a medicine used for treating diabetic complications and diseases caused by oxidative stress. The structure of the compound is shown in a formula I. The preparation method comprises the following steps: firstly reacting substituted benzaldehyde with substituted acetic acid or acid anhydride thereof to obtain substituted cinnamic acid, then reacting with a diamine compound protected by N-tertiary butoxy acyl to obtain substituted cinnamoyl diamide protected by N-tertiary butoxy acyl; and carrying out tertiary butoxy acyl deprotection on the substituted cinnamoyl diamide protected by N-tertiary butoxy acyl, and then reacting with natural or non-natural N-acyl alpha-amino acid, so that the cinnamic acid derivative is obtained. The cinnamic acid derivative compound disclosed by the invention has excellent inhibitory activity on aldose reductase and excellent antioxidant activity and can be applied to preparation of a medicine used for treating the diabetic complications, especially diabetic retinopathy, senile dementia due to diabetes and nerve ending disturbance, as well as diseases caused by the oxidative stress.

POLYMYXIN ANALOGS USEFUL AS ANTIBIOTIC POTENTIATORS

The disclosure provides compounds of the formula (I) or a tautomer thereof, or a pharmaceutically acceptable salt of either of the foregoing. The variables A, R1, and R2 are defined in the disclosure. The disclosure further includes pharmaceutical compositions comprising a compound of formula I together with at least one pharmaceutically acceptable carrier. The disclosure also includes a method of sensitizing bacteria to an antibacterial agent, comprising administering to a patient infected with the bacteria, simultaneously or sequentially, a therapeutically effective amount of the antibacterial agent and a compound of formula (I).

Process improvements for the preparation of kilo quantities of a series of isoindoline compounds

A series of isoindoline analogues with either an indazole (HMR 2934, HMR 2651) or benzisoxazole (HMR 2543) appendage were prepared for the proposed treatment of psychiatric disorders such as obsessive compulsive disorder and attention deficit disorder. The isoindoline compounds were prepared by reduction of the corresponding phthalimides with LiAlH4. One compound was not chiral, and the other two required an enantioselective synthesis. The key step for these optically active analogues involved the coupling by an SN2 process of either a piperazynyl intermediate or a piperdinyl intermediate with methyl 3-benzyloxy-2-trifluoromethansulfonatopropionate. The products for these two analogues had >98% ee. Process improvements led to the multi-kilogram syntheses of each of these compounds.