56926-94-4

Basic information

• Product Name: BOC-SER(TOS)-OCH3
• Synonyms: BOC-L-SER(OTS)-OME;BOC-SER(TOS)-OCH3;BOC-SER(TOS)-OME;Boc-L-Ser(Tos)-OCH3;(S)-methyl 2-(tert-butoxycarbonylamino)-3-(tosyloxy)propanoate;REF DUPL: Boc-Ser(Tos)-OMe;Methyl (2S)-2-[N-(t-butoxycarbonyl)aMino]-3-(4-Methylbenzenesulfonyl)-oxypropionate;Methyl (2S)-2-[N-(tert-butoxycarbonyl)amino]-3-[[(4-methylphenyl)sulfonyl]oxy]propionate
• CAS NO: 56926-94-4
• Molecular Formula: C₁₆H₂₃NO₇S
• Molecular Weight: 373.42
• Product Categories: Amino Acid Derivatives;Boc-Amino Acids and Derivative;Boc-Amino acid series
• Mol File: 56926-94-4.mol
• Article Data: 24

Chemical Properties

• Melting Point: 74-75℃
• Boiling Point: 520 °C at 760 mmHg
• Flash Point: 268.3 °C
• Appearance: /
• Density: 1.236
• Vapor Pressure: 6.48E-11mmHg at 25°C
• Refractive Index: 1.514
• Storage Temp.: 2-8°C
• CAS DataBase Reference: BOC-SER(TOS)-OCH3(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-SER(TOS)-OCH3(56926-94-4)
• EPA Substance Registry System: BOC-SER(TOS)-OCH3(56926-94-4)

Safety Data

• Hazardous Substances Data: 56926-94-4(Hazardous Substances Data)

Usage

General Description

BOC-SER(TOS)-OCH3, also known as Boc-Ser(Tos)-OMe, is a chemical compound frequently used in the field of peptide synthesis. It falls under the category of protected amino acids, specifically a derivative of serine, which means it's used to prevent unwanted side reactions during the process of creating peptides. The BOC, or tert-butyloxycarbonyl, group shields the amine group of the serine amino acid, while the TOS, or tosylate, group protects the hydroxyl side chain. The OCH3, or methoxy, group indicates methylation, which makes the compound less reactive, aiding in the process of peptide coupling. In summary, BOC-SER(TOS)-OCH3 is a protectant molecule used in the synthesis of peptides.

InChI:InChI=1/C16H23NO7S/c1-11-6-8-12(9-7-11)25(20,21)23-10-13(14(18)22-5)17-15(19)24-16(2,3)4/h6-9,13H,10H2,1-5H3,(H,17,19)/t13-/m0/s1

Upstream product

• 2766-43-0 N-tert-butyloxycarbonyl-L-serine methyl ester 
• 1939-99-7 benzenesulfonyl chloride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 3262-72-4 (S)-N-(tert-butoxycarbonyl)serine 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 116611-42-8 (R)-2-tert-butoxycarbonylamino-3-phenylsulfanylpropionic acid methyl ester 
• 175844-11-8 methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-bromopropionate 
• 869646-27-5 N-Boc-L-Sec(4-MeBzl)-OH 
• 1009373-07-2 methyl (2R)-2-[N-(t-butoxycarbonyl)amino]-3-(4-phenoxy)thiophenoxypropionate 
• 122225-54-1 (S)-3-azido-2-((tert-butoxycarbonyl)amino)propanoic acid 
• 97651-96-2 (S)-methyl 2-[(tert-butoxycarbonyl)amino]-3-(4-phenyl-1H-1,2,3-triazol-1-yl)propanoate 
• 922178-77-6 2-tert-butoxycarbonylamino-3-(4-methyl-benzylselanyl)-propionic acid methyl ester 
• 55477-80-0 methyl 2-[(tert-butoxycarbonyl)amino]acrylate 
• 87974-77-4 methyl (2S)-2-tert-butoxycarbonylaminohexanoate 
• 116611-59-7 D-N-Boc-nor-leucine methyl ester 
• 116611-51-9 [(R)-2-Benzenesulfonyl-3-phenyl-1-(tetrahydro-pyran-2-yloxymethyl)-propyl]-carbamic acid tert-butyl ester 
• 116611-53-1 [(R)-2-Benzenesulfonyl-1-(tetrahydro-pyran-2-yloxymethyl)-pentyl]-carbamic acid tert-butyl ester 
• 116611-52-0 [(R)-2-Benzenesulfonyl-1-(tetrahydro-pyran-2-yloxymethyl)-butyl]-carbamic acid tert-butyl ester 
• 116611-60-0 ((R)-2-Benzenesulfonyl-1-hydroxymethyl-3-phenyl-propyl)-carbamic acid tert-butyl ester 

Relevant articles and documents

Biosynthesis of the antibiotic tropodithietic acid by the marine bacterium Phaeobacter inhibens

The biosynthesis of tropodithietic acid was investigated using a combinatorial approach of feeding experiments, gene knockouts and bioinformatic analyses. The mechanism of sulfur introduction is distinct from known mechanisms in holomycin, thiomarinol A a

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.

FUSED HETEROCYCLIC BENZODIAZEPINE DERIVATIVES AND USES THEREOF

The present disclosure provides compounds and compositions capable of extending lifespan, and methods of use thereof.