1492-52-0

Basic information

• Product Name: Z-SER(TOS)-OME
• Synonyms: N^a-Benzyloxycarbonyl-O-(p-toluenesulfonyl)-L-serine Methyl ester, 98%;Methyl (S)-2-[(benzyloxycarbonyl)amino]-3-(p-toluenesulfonyloxy)propanoate;O-[(4-Methylphenyl)sulfonyl]-N-[(phenylmethoxy)carbonyl]-L-serine methyl ester;L-Serine,O-[(4-Methylphenyl)sulfonyl]-N-[(phenylMethoxy)carbonyl]-, Methyl ester;-OMe;Z-Ser(Tos);Z-L-Ser(Tos)-OMe;Z-O-4-toluenesulfonyl-L-serine methyl ester99%
• CAS NO: 1492-52-0
• Molecular Formula: C₁₉H₂₁NO₇S
• Molecular Weight: 407.44
• Product Categories: Z-Amino Acids and Derivatives;Z-Amino acid series
• Mol File: 1492-52-0.mol

Chemical Properties

• Boiling Point: 589.3°C at 760 mmHg
• Flash Point: 310.2°C
• Appearance: /
• Density: 1.3g/cm³
• Vapor Pressure: 7.23E-14mmHg at 25°C
• Refractive Index: 1.563
• Storage Temp.: -15°C
• CAS DataBase Reference: Z-SER(TOS)-OME(CAS DataBase Reference)
• NIST Chemistry Reference: Z-SER(TOS)-OME(1492-52-0)
• EPA Substance Registry System: Z-SER(TOS)-OME(1492-52-0)

Safety Data

• Hazardous Substances Data: 1492-52-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Z-SER(TOS)-OME is used as a protecting group for serine amino acids during chemical reactions to ensure their selective manipulation and prevent unwanted side reactions.
Used in Peptide Synthesis:
In the field of peptide synthesis, Z-SER(TOS)-OME is utilized as a key component to control the reactivity and specificity of serine amino acids, facilitating the assembly of peptide sequences with desired properties.
Used in Pharmaceutical Development:
Z-SER(TOS)-OME serves as a building block in the creation of complex molecules and pharmaceutical drugs, contributing to the development of new therapeutic agents with improved efficacy and selectivity.
Used in Chemical Product Development:
Z-SER(TOS)-OME plays a significant role in the production of various chemical products, where its protective properties allow for the synthesis of molecules with specific functionalities and reactivities.

InChI:InChI=1/C19H21NO7S/c1-14-8-10-16(11-9-14)28(23,24)27-13-17(18(21)25-2)20-19(22)26-12-15-6-4-3-5-7-15/h3-11,17H,12-13H2,1-2H3,(H,20,22)/t17-/m0/s1

Upstream product

• 501-53-1 benzyl chloroformate 
• 1145-80-8 N-(benzyloxycarbonyl)-L-serine 
• 1676-81-9 N-benzyloxycarbonyl-L-serine methyl ester 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 56877-40-8 Z-γ,γ,-di-tert-butyl-D,L-carboxyglutamic acid methyl ester 
• 56926-92-2 2-(2-Benzyloxycarbonylamino-2-hydrazinocarbonyl-ethyl)-malonic acid di-tert-butyl ester 
• 39692-63-2 2-benzyloxycarbonylamino-acrylic acid 
• 153277-33-9 N-benzyloxycarbonyl-S-phenyl-L-cysteine methyl ester 
• 21149-17-7 methyl 2-(benzyloxycarbonylamino)acrylate 
• 56926-93-3 2-[2-Benzyloxycarbonylamino-2-(ethoxycarbonylmethyl-carbamoyl)-ethyl]-malonic acid di-tert-butyl ester 
• 56877-43-1 Z-DL-Gla(OtBu)2-OH 
• 56877-43-1 N-(benzyloxycarbonyl)-γ,γ-di-tert-butyl-D-γ-carboxyglutamic acid 
• 60686-50-2 N-(benzyloxycarbonyl)-γ,γ-di-tert-butyl-L-γ-carboxyglutamic acid 
• 397243-75-3 (R)-2-Benzyloxycarbonylamino-3-(4-phenoxy-benzenesulfonyl)-propionic acid methyl ester 
• 78553-47-6 methyl (2S)-2-[N-(benzyloxycarbonyl)amino]pent-4-enoate 
• 97551-67-2 (3S,5S)-3-benzyloxycarbonylamino-5-hydroxy-γ-lactone 
• 112741-66-9 (2S,4R)-2-[(benzyloxycarbonyl)amino]-4-(hydroxymethyl)butyric acid γ-lactone 
• 200344-43-0 methyl R(S)-3-diphenylphosphanylmethyl-N-carbobenzyloxyserinate 

Relevant articles and documents

Utility of tetrathiomolybdate and tetraselenotungstate: Efficient synthesis of cystine, selenocystine, and their higher homologues

Efficient synthesis of cystine, selenocystine, and their higher homologues like homo and bishomo amino acid derivatives from natural amino acid derivatives using tetrathiomolybdate and tetraselenotungstate reagents under mild and neutral conditions is reported. The generality of the reaction has been studied by capping various groups to amino and carboxyl components of canonical amino acids.

Synthesis of new 3- and 4-substituted analogues of acyl homoserine lactone quorum sensing autoinducers

The quorum sensing mechanism in Gram-negative bacteria uses small intercellular signal molecules, N-acyl-homoserine lactones (AHLs), to control transcription of specific genes in relation to population density. In this communication, we describe the parallel synthesis of new AHL analogues, in which substituents have been introduced into the 3- and 4-positions of the lactone ring. These analogues have been screened for their ability to activate and inhibit a Vibrio fischeri LuxI/LuxR-derived quorum sensing reporter system.

α-Amino-β-sulphone hydroxamates as potent MMP-13 inhibitors that spare MMP-1

A series of α-amino-β-sulphone hydroxamates was prepared and evaluated for potency versus MMP-13 and selectivity versus MMP-1. Various substituents were employed on the α-amino group (P1 position), as well as different groups attached to the su