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

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

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.

Synthesis and biochemical evaluation of Aminopropanolyl-Thymine tri-Phosphate (ap-TTP)

Deoxyribonucleoside triphosphates (dNTPs) are building blocks for the biosynthesis of DNA. Various modified dNTPs’ analogs have synthesized by structural changes of nucleoside’s susgar and nucleobases and employed for synthesis of modified DNA. A very few modified dNTPs have prepared from non-sugar nucleoside analogs. This report describes the synthesis of acyclic nucleoside triphosphate (NTP) analog from amino acid L-Serine as aminopropanolyl-thymine triphosphate (ap-TTP) and demonstrate its biochemical evaluation as enzymatic incorporation of ap-TTP into DNA with DNA polymerases with primer extension methods. Alanyl peptide nucleicacids (Ala-PNA) are the analogs of DNA which contains alanyl backbone. Aminopropanolyl–analogs are derivatives of alanyl back bone. Ap-TTP analog is nucleoside triphosphate analog derived from Ala-PNA. Importantly, this report also sheds light on the crystal packing arrangement of alaninyl thymine ester derivative in solid-state and reveals the formation of self-duplex assembly in anti-parallel fashion via reverse Watson-Crick hydrogen bonding and π–π interactions. Hence, ap-TTP is a useful analog which also generates the free amine functional group at the terminal of DNA oligonucleotide after incorporation.

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.

Me3SI-promoted chemoselective deacetylation: a general and mild protocol

A Me3SI-mediated simple and efficient protocol for the chemoselective deprotection of acetyl groups has been developedviaemploying KMnO4as an additive. This chemoselective deacetylation is amenable to a wide range of substrates, tolerating diverse and sensitive functional groups in carbohydrates, amino acids, natural products, heterocycles, and general scaffolds. The protocol is attractive because it uses an environmentally benign reagent system to perform quantitative and clean transformations under ambient conditions.

Synthesis and Biological Evaluation of CF3Se-Substituted α-Amino Acid Derivatives

Several CF3Se-substituted α-amino acid derivatives, such as (R)-2-amino-3-((trifluoromethyl)selanyl)propanoates (5 a/6 a), (S)-2-amino-4-((trifluoromethyl)selanyl)butanoates (5 b/6 b), (2R,3R)-2-amino-3-((trifluoromethyl)selanyl)butanoates (5 c/6 c), (R)-2-((S)-2-amino-3-phenylpropanamido)-3-((trifluoromethyl)selanyl)propanoates (11 a/12 a), and (R)-2-(2-aminoacetamido)-3-((trifluoromethyl)selanyl)propanoates (11 b/12 b), were readily synthesized from natural amino acids and [Me4N][SeCF3]. The primary in vitro cytotoxicity assays revealed that compounds 6 a, 11 a and 12 a were more effective cell growth inhibitors than the other tested CF3Se-substituted derivatives towards MCF-7, HCT116, and SK-OV-3 cells, with their IC50 values being less than 10 μM for MCF-7 and HCT116 cells. This study indicated the potentials of CF3Se moiety as a pharmaceutically relevant group in the design and synthesis of novel biologically active molecules.

Efficient Hydro- and Organogelation by Minimalistic Diketopiperazines Containing a Highly Insoluble Aggregation-Induced, Blue-Shifted Emission Luminophore**

We report the synthesis, gelation abilities and aggregation-induced, blue-shifted emission (AIBSE) properties of two minimalistic diketopiperazine-based gelators. Despite containing a highly insoluble luminophore that makes up more than half of their respective molecular masses, efficient hydrogelation by multiple stimuli for one and efficient organogelation for the other compound are reported. Insights into the aggregation and gelation properties were gained through examination of the photophysical and material properties of selected gels, which are representative of the different modes of gelation. The synthesis of the gelators is highly modular and based on readily available amino acid building blocks, allowing the efficient and rapid diversification of these core structures and fine-tuning of gel properties.

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.

Late-Stage Intermolecular Allylic C-H Amination

Allylic amination enables late-stage functionalization of natural products where allylic C-H bonds are abundant and introduction of nitrogen may alter biological profiles. Despite advances, intermolecular allylic amination remains a challenging problem due to reactivity and selectivity issues that often mandate excess substrate, furnish product mixtures, and render important classes of olefins (for example, functionalized cyclic) not viable substrates. Here we report that a sustainable manganese perchlorophthalocyanine catalyst, [MnIII(ClPc)], achieves selective, preparative intermolecular allylic C-H amination of 32 cyclic and linear compounds, including ones housing basic amines and competing sites for allylic, ethereal, and benzylic amination. Mechanistic studies support that the high selectivity of [MnIII(ClPc)] may be attributed to its electrophilic, bulky nature and stepwise amination mechanism. Late-stage amination is demonstrated on five distinct classes of natural products, generally with >20:1 site-, regio-, and diastereoselectivity.

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.

Synthesis and Biological Evaluation of a Library of AGE-Related Amino Acid Triazole Crosslinkers

Three N-Boc-protected amino acids, l-serine, l-aspartic, and l-glutamic acid, were either converted into their methyl azidoalkanoates or various alkynes via Bestmann-Ohira strategy or via reaction with propargylamine and propargyl bromide, respectively. The Cu-catalyzed click reaction provided a library of amino acid based triazoles, which were further N-methylated to triazolium iodides or deprotected and precipitated as free amino acid triazole dihydrochlorides. The biological properties of all derivatives were investigated by cytotoxicity assay (against L929 mouse fibroblasts) and broth microdilution method (E. coli ΔTolC and S. aureus). First results reveal complete inactivity for triazolium iodides with cell viabilities and microbial growths nearly 100 %, indicating them as possible analogs of advanced glycation endproducts (AGEs).