2766-43-0

Basic information

• Product Name: Boc-L-serine methyl ester
• Synonyms: BOC-L-SERINE METHYL ESTER;BOC-SERINE-OME;BOC-SER-OME;N-ALPHA-T-BUTOXYCARBONYL-L-SERINE METHYL ESTER;N-BOC-L-SERINE METHYL ESTER;N-(TERT-BUTOXYCARBONYL)-L-SERINE METHYL ESTER;Butoxycarbonylserinemethylester;N-T-BOC-L-SERINE METHYL ESTER
• CAS NO: 2766-43-0
• Molecular Formula: C₉H₁₇NO₅
• Molecular Weight: 219.23
• EINECS: 1533716-785-6
• Product Categories: Amino Acid Derivatives;Serine [Ser, S];Boc-Amino Acids and Derivative;Amino Acids;Amino Acids (N-Protected);Biochemistry;Boc-Amino Acids;Boc-Amino acid series
• Mol File: 2766-43-0.mol
• Article Data: 147

Chemical Properties

• Boiling Point: 354.3 °C at 760 mmHg
• Flash Point: >230 °F
• Appearance: Colorless to yellow/Liquid or Oil
• Density: 1.082 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.94E-06mmHg at 25°C
• Refractive Index: n20/D 1.452(lit.)
• Storage Temp.: -15°C
• PKA: 10.70±0.46(Predicted)
• Water Solubility: Slightly soluble in water.
• BRN: 3545389
• CAS DataBase Reference: Boc-L-serine methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-L-serine methyl ester(2766-43-0)
• EPA Substance Registry System: Boc-L-serine methyl ester(2766-43-0)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• Hazardous Substances Data: 2766-43-0(Hazardous Substances Data)

Usage

Description

Boc-L-serine methyl ester, also known as N-tert-Butoxycarbonyl-L-serine Methyl Ester, is an amino acid derivative derived from L-Serine Methyl Ester Hydrochloride. It is characterized by its liquid chemical properties and is used in various applications due to its unique structure and reactivity.

Uses

Used in Biomedical Polymers:
Boc-L-serine methyl ester is used as a building block for the synthesis of new biomedical polymers that incorporate Serine and Threonine side groups. These polymers have potential applications in the development of biomaterials, drug delivery systems, and tissue engineering due to their biocompatibility and ability to mimic natural biological structures.
Used in Tn Antigen Preparation:
Boc-L-serine methyl ester serves as a key component in the preparation of Tn antigen, a carbohydrate antigen that is often overexpressed in various types of cancer cells. Its role in the synthesis of Tn antigen makes it a valuable compound in the field of cancer research and the development of cancer diagnostic tools.
Used in L-Glutamic Acid p-Nitroanilide Analogs:
Boc-L-serine methyl ester is utilized in the preparation of L-glutamic acid p-nitroanilide analogs, which are compounds that have potential applications in the development of new drugs and therapeutic agents. These analogs can be used to study the activity of enzymes and other biological processes, contributing to the advancement of pharmaceutical research.

InChI:InChI=1/C9H17NO5/c1-9(2,3)15-8(13)10-6(5-11)7(12)14-4/h6,11H,5H2,1-4H3,(H,10,13)/t6-/m0/s1

Upstream product

• 186581-53-3 diazomethane 
• 3262-72-4 (S)-N-(tert-butoxycarbonyl)serine 
• 67-56-1 methanol 
• 2788-84-3 (S)-serine methyl ester 
• 34619-03-9 tert-butyldicarbonate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 5680-80-8 methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride 
• 108655-53-4 1-t-butoxycarbonyl-v-triazolo<4,5-b>pyridine 
• 54555-84-9 benzyl iodoethyl ether 
• 74-88-4 methyl iodide 
• 56-45-1 L-serin 
• 126645-26-9 (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)propanoate 
• 404586-94-3 1-(tert-butoxy)-2-(tert-butoxy)carbonyl-1,2-dihydroisoquinoline 
• 88099-67-6 methyl (2S)-2-(dibenzylamino)-3-hydroxypropanoate 

Downstream Products

• 2766-42-9 tert-butyl (S)-(1-hydrazineyl-3-hydroxy-1-oxopropan-2-yl)carbamate 
• 1026330-12-0 (S)-3-[Bis-(4-chloro-benzyloxy)-phosphanyloxy]-2-tert-butoxycarbonylamino-propionic acid methyl ester 
• 55477-80-0 methyl 2-[(tert-butoxycarbonyl)amino]acrylate 
• 97651-96-2 (S)-methyl 2-[(tert-butoxycarbonyl)amino]-3-(4-phenyl-1H-1,2,3-triazol-1-yl)propanoate 
• 56926-94-4 methyl (2S)-2-[N-(t-butoxycarbonyl)amino]-3-(4-methylbenzenesulfonyl)-oxypropionate 
• 95715-86-9 (S)-2,2-dimethyl-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl ester 
• 108149-60-6 methyl [(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]carboxylate 
• 134167-07-0 (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-methoxypropanoate 
• 159846-14-7 methyl (2S)-3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)-2-[(tert-butoxy)carbonylamino]propanoate 
• 169515-95-1 (R)-2-tert-Butoxycarbonylamino-3-[5-(4-fluoro-phenyl)-4-(4-methanesulfonyl-phenyl)-thiophen-2-ylsulfanyl]-propionic acid methyl ester 
• 116611-42-8 (R)-2-tert-butoxycarbonylamino-3-phenylsulfanylpropionic acid methyl ester 
• 175844-11-8 methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-bromopropionate 
• 169515-92-8 (R)-2-Acetylamino-3-[5-(4-fluoro-phenyl)-4-(4-methanesulfonyl-phenyl)-thiophen-2-ylsulfanyl]-propionic acid 
• 2788-84-3 (S)-serine methyl ester 

Relevant articles and documents

Stereoselective synthesis of (-)-α-kainic acid and (+)-α-allokainic acid via trimethylstannyl-mediated radical carbocyclization and oxidative destannylation

(-)-α-Kainic acid (1) and its C4 epimer (+)-α-allokainic acid (2) have been prepared from L-serine. The requisite stereochemical array in (-)-α-kainic acid (1) was introduced using a trimethylstannyl radical carbocyclization of a diene, which gave the 2,3-trans/3,4-cis and 2,3-trans/3,4-trans componnds in a 2.8:1 ratio and in high yield. The destannylation of the trisubstituted pyrrolidine nucleus was achieved via an oxidative cleavage of the C-Sn bond with ceric ammonium nitrate. This provided a dimethyl acetal that was further transformed into the intended α-kainic acid. When the same radical carbocyclization was attempted on a triene, the 2,3-trans/3,4-trans and the 2,3-trans/3,4-cis adducts were obtained in a 2.5:1 ratio, respectively. This approach was used to synthesize (+)-α-allokainic acid.

Simple and efficient procedure for a multigram synthesis of both trans - And cis -1-Amino-2-(trifluoromethyl)cyclopropane-1-carboxylic Acid

A simple and efficient procedure for the multigram synthesis of both (±)-trans- and (±)-cis-1-amino-2-(trifluoromethyl)cyclopropane-1- carboxylic acid was developed. The key step of the synthesis is the addition of 1-diazo-2,2,2-trifluoroethane to methyl 2-[(tert-butoxycarbonyl)amino]acrylate, followed by thermal decomposition of the resulting pyrazoline. Gram quantities of trans- and cis-1-amino-2-(trifluoromethyl)cyclopropane-1-carboxylic acid were easily prepared from l-serine in one synthetic run. Georg Thieme Verlag Stuttgart - New York.

Biocompatible Photoinduced Alkylation of Dehydroalanine for the Synthesis of Unnatural α-Amino Acids

A site-selective alkylation of dehydroalanine to access protected unnatural amino acids is described. The protocol is characterized by the wide nature of alkyl radicals employed, mild conditions, and functional group compatibility. This protocol is further extended to access peptides, late-stage functionalization of pharmaceuticals, and enantioenriched amino acids.

Alcohol functionality in the fatty acid backbone of sphingomyelin guides the inhibition of blood coagulation

Cell-surface sphingomyelin (SM) inhibits binary and ternary complex activity of blood coagulation by an unknown mechanism. Here we show the OH functionality of SM contributes in forming the close assembly through intermolecular H-bond and through Ca2+ chelation, which restricts the protein-lipid/protein-protein interactions and thus inhibits the coagulation procedure.