4-(((((9H-fluoren-9-yl)methoxy)carbonyl)oxy)methyl)benzyl (Z)-2,2,2-trifluoro-N-phenylacetimidate

4-(((((9H-Fluoren-9-yl)methoxy)carbonyl)oxy)methyl)benzyl (Z)-2,2,2-trifluoro-N-phenylacetimidate 4-(((((9H-Fluoren-9-yl)methoxy)carbonyl)oxy)methyl)benzyl (Z)-2,2,2-trifluoro-N-phenylacetimidate is a synthetic organic compound combining an Fmoc-protected benzyl group with a trifluoroacetimidate ester. Below is its detailed structural and functional analysis: Structural Breakdown Core components : Fmoc-protected benzyl group : A 4-substituted benzyl alcohol derivative with a ((9H-fluoren-9-yl)methoxy)carbonyloxy (Fmoc-O-CO-O-) group at the para position. The Fmoc group (fluorenylmethoxycarbonyl) acts as a base-labile protecting group, commonly used in peptide synthesis. (Z)-2,2,2-Trifluoro-N-phenylacetimidate : An imidate ester with: A trifluoromethyl group (CF₃) at the α-position. A phenyl group attached to the imine nitrogen. (Z)-stereochemistry at the C=N bond. Key features : Molecular formula : Estimated as C₃₇H₂₈F₃NO₅ (exact mass requires experimental verification). Functional groups : Carbonate ester (linking Fmoc to benzyl). Imidate ester (trifluoroacetimidate). Aromatic rings (fluorenyl, benzyl, and phenyl). Synthesis and Reactivity Likely synthesized via: Fmoc protection : Reaction of 4-(hydroxymethyl)benzyl alcohol with Fmoc-Cl (or Fmoc-Oxyma) to form the carbonate linkage. Imidate formation : Condensation of trifluoroacetimidic acid with the activated benzyl alcohol intermediate under acidic conditions, favoring (Z)-geometry. Reactivity : Fmoc group removable with piperidine or DBU in DMF. Imidate ester acts as a leaving group in nucleophilic substitutions or cross-couplings. Applications Protecting group strategy : Temporary protection of hydroxyl groups during solid-phase synthesis. Orthogonal deprotection (Fmoc vs. imidate). Trifluoromethyl chemistry : Potential use in introducing CF₃ groups into pharmaceuticals or agrochemicals. Physicochemical Properties Solubility : Likely soluble in polar aprotic solvents (DMF, DCM) due to Fmoc and aromatic groups. Stability : Sensitive to bases (Fmoc cleavage). Hydrolytically unstable under acidic or aqueous conditions (imidate ester). Safety Considerations Hazards : Irritant (common with Fmoc derivatives). Possible respiratory sensitizer (imidate esters). Handling : Use PPE (gloves, goggles) and work in a fume hood. This compound exemplifies a bifunctional reagent with applications in targeted drug delivery and fluorinated molecule synthesis. Its design leverages the stability of Fmoc groups and the reactivity of trifluoroacetimidates for selective transformations. Citations: https://pubchem.ncbi.nlm.nih.gov/compound/Fmoc-4-Amb-OH https://pubchem.ncbi.nlm.nih.gov/compound/Fmoc-Glu-OBzl https://www.ambeed.com/products/1313054-32-8.html https://pubchem.ncbi.nlm.nih.gov/compound/352523-15-0 https://pubchem.ncbi.nlm.nih.gov/compound/155819748 https://www.tcichemicals.com/assets/cms-pdfs/ReagentGuide_8th_SynthesticOrganicChemistry_MaterialsChemistry.pdf https://www.pharmaffiliates.com/en/2088577-19-7-4-methylphenyl-2-o-benzoyl-3-6-di-o-benzyl-4-o-9-fluorenylmethoxycarbonyl-1-thio-beta-d-galactopyranoside-pa270026106.html https://www.sigmaaldrich.com/IN/en/product/bldpharmatechcoltd/bl3h9aa4ff6d?context=bbe