82911-81-7

Basic information

• Product Name: benzyl N-(2,2,2-trichloroethoxycarbonyl)-L-serine
• Synonyms: benzyl N-(2,2,2-trichloroethoxycarbonyl)-L-serine
• CAS NO: 82911-81-7
• Molecular Weight: 370.617
• Mol File: 82911-81-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: benzyl N-(2,2,2-trichloroethoxycarbonyl)-L-serine(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl N-(2,2,2-trichloroethoxycarbonyl)-L-serine(82911-81-7)
• EPA Substance Registry System: benzyl N-(2,2,2-trichloroethoxycarbonyl)-L-serine(82911-81-7)

Safety Data

• Hazardous Substances Data: 82911-81-7(Hazardous Substances Data)

Upstream product

• 100-51-6 benzyl alcohol 
• 66065-85-8 succinimidyl 2,2,2-trichloroethyl carbonate 
• 60022-62-0 L-serine benzyl ester hydrochloride 
• 1738-72-3 L-serine benzyl ester 

Downstream Products

• 640291-21-0 benzyl N-trichloroethoxycarbonyl-O-[3,4,6-tri-O-acetyl-2-N-trichloroethoxycarbonyl-β-D-glucopyranosyl]-L-serinate 
• 173029-46-4 N-trichloroethoxycarbonyl O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1<*>4)-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-L-serine benzyl ester 
• 173029-39-5 N-trichloroethoxycarbonyl-O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-L-serine benzyl ester 
• 197663-21-1 N-trichloroethoxycarbonyl-3-O-(3,4-di-O-acetyl-2-azido-2-deoxy-6-O-triphenylmethyl-α-D-galactopyranosyl)-L-serine benzyl ester 
• 197663-13-1 N-trichloroethoxycarbonyl-3-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-L-serine benzyl ester 
• 197663-24-4 O--(2->6)-O-(2-acetamido-3,4-di-O-acetyl-2-deoxy-α-D-galactopyranosyl)-(1->3)-N-(trichloroethoxycarbonyl)-L-serine benzyl ester 
• 197663-22-2 N-trichloroethoxycarbonyl-3-O-(2-acetamido-3,4-di-O-acetyl-2-deoxy-6-O-triphenylmethyl-α-D-galactopyranosyl)-L-serine benzyl ester 
• 197663-15-3 N-trichloroethoxycarbonyl-3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-seryl-(N'-benzyloxycarbonylaminoethyl)amide 
• 197663-14-2 N-trichloroethoxycarbonyl-3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-serine benzyl ester 
• 197663-23-3 N-trichloroethoxycarbonyl-3-O-(2-acetamido-3,4-di-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-serine benzyl ester 
• 197663-25-5 O--(2->6)-O-(2-acetamido-3,4-di-O-acetyl-2-deoxy-α-D-galactopyranosyl)-(1->3)-N-(trichloroethoxycarbonyl)-L-serine-(N'-benzyloxycarbonylaminoethyl)... 

Relevant articles and documents

Self-Adjuvanting Cancer Vaccines from Conjugation-Ready Lipid A Analogues and Synthetic Long Peptides

Self-adjuvanting vaccines, wherein an antigenic peptide is covalently bound to an immunostimulating agent, have been shown to be promising tools for immunotherapy. Synthetic Toll-like receptor (TLR) ligands are ideal adjuvants for covalent linking to peptides or proteins. We here introduce a conjugation-ready TLR4 ligand, CRX-527, a potent powerful lipid A analogue, in the generation of novel conjugate-vaccine modalities. Effective chemistry has been developed for the synthesis of the conjugation-ready ligand as well as the connection of it to the peptide antigen. Different linker systems and connection modes to a model peptide were explored, and in vitro evaluation of the conjugates showed them to be powerful immune-activating agents, significantly more effective than the separate components. Mounting the CRX-527 ligand at the N-terminus of the model peptide antigen delivered a vaccine modality that proved to be potent in activation of dendritic cells, in facilitating antigen presentation, and in initiating specific CD8+ T-cell-mediated killing of antigen-loaded target cells in vivo. Synthetic TLR4 ligands thus show great promise in potentiating the conjugate vaccine platform for application in cancer vaccination.

Introduction of 9-fluorenylmethyloxycarbonyl, trichloroethoxycarbonyl, and benzyloxycarbonyl amine protecting groups into O-unprotected hydroxyamino acids using succinimidyl carbonates

9-Fluorenylmethyl succinimidyl, pentachlorophenyl, and benzotriazole-1-yl carbonates were prepared and their reactivity with L-serine and L-serine benzyl ester was compared.The most efficient reagent, 9-fluorenylmethyl succinimidyl carbonate, was used for the preparation of 9-flourenylmethyloxycarbonyl derivatives of other hydroxyamino acids and hydroxyamino acid esters in high yields.The use of trichloroethyl and benzyl succinimidyl carbonates for an efficient conversion of hydroxyamino acids and their esters into the corresponding N-trichloroethoxycarbonyl and benzyloxycarbonyl derivatives is described.