100938-55-4

Basic information

• Product Name: N-(9H-fluorene-9-yl)-methoxycarbonyl-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester
• Synonyms: N-(9H-fluorene-9-yl)-methoxycarbonyl-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester
• CAS NO: 100938-55-4
• Molecular Weight: 744.755
• Mol File: 100938-55-4.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: N-(9H-fluorene-9-yl)-methoxycarbonyl-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-(9H-fluorene-9-yl)-methoxycarbonyl-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester(100938-55-4)
• EPA Substance Registry System: N-(9H-fluorene-9-yl)-methoxycarbonyl-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester(100938-55-4)

Safety Data

• Hazardous Substances Data: 100938-55-4(Hazardous Substances Data)

Upstream product

• 67817-41-8 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl chloride 
• 73724-48-8 N-(fluoren-9-ylmethoxycarbonyl)-L-threonine benzyl ester 
• 100-39-0 benzyl bromide 
• 73731-37-0 Fmoc-Thr-OH 
• 84278-00-2 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose 
• 197663-12-0 phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thiol-D-galactopyranoside 
• 167939-15-3 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-galactopyranosyl trichloroacetimidate 
• 150809-76-0 phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-seleno-α-D-galactopyranoside 
• 213331-76-1 (2S,3R)-3-((3aR,4R,6S,7R,7aR)-7-Azido-2,2-dimethyl-4-triisopropylsilanyloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester 
• 68733-26-6 2-deoxy-2-azidogalactopyranose 
• 1772-03-8 D-(+)-galactosamine hydrochloride 
• 148416-94-8 phenyl-3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thio-β-D-galactopyranoside 
• 68733-27-7 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl iodide 
• 67673-39-6 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl bromide 

Downstream Products

• 100938-56-5 N^α-fluoren-9-ylmethoxycarbonyl-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-galactopyranosyl)-L-threoninebenzyl ester 
• 116783-35-8 N-(9H-fluoren-9-yl)methoxycarbonyl-O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-threonine 
• 1426832-55-4 C₄₈H₅₇N₃O₁₆ 
• 1436867-96-7 C₂₀H₃₃N₃O₁₀ 
• 1426832-53-2 c[L-aspartyl-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-threonyl] 
• 100929-15-5 N,O-diacetyl-L-seryl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galctopyranosyl)-L-seryl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-threonine benzylester 
• 129415-19-6 C₄₅H₆₃N₅O₂₃ 
• 129432-11-7 N-<2-(4-pyridyl)ethoxycarbonyl>-L-alanyl-L-alanyl-O-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester 
• 100929-13-3 N-<2-(4-pyridyl)ethoxycarbonyl>-L-seryl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-seryl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester 
• 137816-30-9 O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-N^α-(fluoren-9-ylmethoxycarbonyl)-L-threonine pentafluorophenyl ester 
• 218291-45-3 C₅₈H₇₀N₄O₂₃ 

Relevant articles and documents

Activation of glycosyl trichloroacetimidates with perchloric acid on silica (HClO4-SiO2) provides enhanced α-selectivity

Obtaining high stereoselectivity in glycosylation reactions is often challenging in the absence of neighboring group participation. In this study, we demonstrate that activation of glycosyl trichloroacetimidate donors with immobilized perchloric acid on s

A Synthetic MUC1 Glycopeptide Bearing βGalNAc-Thr as a Tn Antigen Isomer Induces the Production of Antibodies against Tumor Cells

This study presents the synthesis of the novel protected O-glycosylated amino acid derivatives 1 and 2, containing βGalNAc-SerOBn and βGalNAc-ThrOBn units, respectively, as mimetics of the natural Tn antigen (αGalNAc-Ser/Thr), along with the solid-phase assembly of the glycopeptides NHAcSer-Ala-Pro-Asp-Thr[αGalNAc]-Arg-Pro-Ala-Pro-Gly-BSA (3-BSA) and NHAcSer-Ala-Pro-Asp-Thr[βGalNAc]-Arg-Pro-Ala-Pro-Gly-BSA (4-BSA), bearing αGalNAc-Thr or βGalNAc-Thr units, respectively, as mimetics of MUC1 tumor mucin glycoproteins. According to ELISA tests, immunizations of mice with βGalNAc-glycopeptide 4-BSA induced higher sera titers (1:320 000) than immunizations with αGalNAc-glycopeptide 3-BSA (1:40 000). Likewise, flow cytometry assays showed higher capacity of the obtained anti-glycopeptide 4-BSA antibodies to recognize MCF-7 tumor cells. Cross-recognition between immunopurified anti-βGalNAc antibodies and αGalNAc-glycopeptide and vice versa was also verified. Lastly, molecular dynamics simulations and surface plasmon resonance (SPR) showed that βGalNAc-glycopeptide 4 can interact with a model antitumor monoclonal antibody (SM3). Taken together, these data highlight the improved immunogenicity of the unnatural glycopeptide 4-BSA, bearing βGalNAc-Thr as Tn antigen isomer.

α-Selective glycosylation affords mucin-related GalNAc amino acids and diketopiperazines active on Trypanosoma cruzi

This work addresses the synthesis and biological evaluation of glycosyl diketopiperazines (DKPs) cyclo[Asp-(αGalNAc)Ser] 3 and cyclo[Asp-(αGalNAc)Thr] 4 for the development of novel anti-trypanosomal agents and Trypanosoma cruzi trans-sialidase (TcTS) inhibitors. The target compounds were synthetized by coupling reactions between glycosyl amino acids αGalNAc-Ser 7 or αGalNAc-Thr 8 and the amino acid (O-tBu)-Asp 17, followed by one-pot deprotection-cyclisation reaction in the presence of 20% piperidine in DMF. The protected glycosyl amino acid intermediates 7 and 8 were, in turn, obtained by α-selective, HgBr2-catalysed glycosylation reactions of Fmoc-Ser/Thr benzyl esters 12/14 with αGalN3Cl 11, being, subsequently, fully deprotected for comparative biological assays. The DKPs 3 and 4 showed relevant anti-trypanosomal effects (IC50 282-124 μM), whereas glycosyl amino acids 1 and 2 showed better TcTS inhibition (57-79%) than the corresponding DKPs (13-25%).