71532-40-6

Usage

Uses

Used in Organic Synthesis:
(9H-fluoren-9-yl)methyl 4-methylbenzenesulfonate is used as a reagent for the synthesis of Se-(9-fluorenylmethyl) selenoesters and amino thioacids. Its application in this context is due to its ability to act as a protecting group, which is crucial for the selective formation of these compounds during the synthesis process. This reagent is particularly valuable in the development of pharmaceuticals and other specialty chemicals where the precise control of chemical reactions is essential.

Upstream product

• 24324-17-2 9-Fluorenylmethanol 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 84888-38-0 (R)-9H-fluorenyl-9-methyl-L-cysteine 
• 84888-34-6 S-Fm-L-cysteine 
• 4425-82-5 9-methylene-fluorene 
• 84888-35-7 N^α-tert-butyloxycarbonyl-(S)-9-fluorenylmethylcysteine 
• 1446274-24-3 (R)-Se-((9H-fluorenyl)methyl) 2-((tert-butoxycarbonyl)amino)-3-phenylpropaneselenoate 
• 1446274-27-6 (S)-benzyl 4-(((9H-fluorenyl)methyl)selanyl)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoate 
• 1446274-29-8 (S)-Se-((9H-fluorenyl)methyl) 2-amino-3-phenylpropaneselenoate trifluoroacetic acid salt 
• 1446274-31-2 (R)-Se-((9H-fluorenyl)methyl) 2-amino-3-phenylpropaneselenoate trifluoroacetic acid salt 
• 1446274-37-8 (S)-benzyl 4-(((9H-fluorenyl)methyl)selanyl)-2-amino-4-oxobutanoate trifluoroacetic acid salt 
• 1446274-38-9 (S)-Se-((9H-fluorenyl)methyl) 2-((S)-2-((tert-butoxycarbonyl)amino)-3-methylbutanamido)-3-phenylpropaneselenoate 
• 1446274-39-0 (R)-Se-((9H-fluorenyl)methyl) 2-((S)-2-((tert-butoxycarbonyl)amino)-3-methylbutanamido)-3-phenylpropaneselenoate 
• 1446274-40-3 (S)-Se-((9H-fluorenyl)methyl) 2-((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanamido)-3-methylbutaneselenoate 
• 1446274-41-4 (S)-Se-((9H-fluorenyl)methyl) 2-((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanamido)propaneselenoate 
• 1446274-42-5 (S)-benzyl 4-(((9H-fluorenyl)methyl)selanyl)-2-((S) 2-((tert-butoxycarbonyl)amino)-3-methylbutanamido)-4-oxobutanoate 

Relevant academic research and scientific papers

Synthesis of macrocyclic and medium-sized ring thiolactonesviathe ring expansion of lactams

A side chain insertion method for the ring expansion of lactams into macrocyclic thiolactones is reported, that can also be incorporated into Successive Ring Expansion (SuRE) sequences. The reactions are less thermodynamically favourable than the analogous lactam- and lactone-forming ring expansion processes (with this notion supported by DFT data), but nonetheless, three complementary protecting group strategies have been developed to enable this challenging transformation to be achieved.

NMR-based assignment of isoleucine: Vs. allo -isoleucine stereochemistry

A simple 1H and 13C NMR spectrometric analysis is demonstrated that permits differentiation of isoleucine and allo-isoleucine residues by inspection of the chemical shift and coupling constants of the signals associated with the proton and carbon at the α-stereocentre. This is applied to the estimation of epimerisation during metal-free N-arylation and peptide coupling reactions.

An assembly concept for the consecutive introduction of unsymmetrical disulfide bonds: Synthesis of a releasable multidrug conjugate of folic acid

(Chemical Equation Presented) We describe the development of methodology which allows for the introduction of a second disulfide bond into a molecular framework with a pre-existing disulfide linker system. Compounds which contain an S-9-fluorenylmethyl-pr

Novel design of bicyclic β-turn dipeptides on solid-phase supports and synthesis of [3.3.0]-bicyclo[2,3]-leu-enkephalin analogues

(Chemical Equation Presented) External bicyclic β-turn dipeptide mimetics provide an excellent design approach that can offer a rich chiral ensemble of structures with different backbone conformations. We report herein a novel design of a convergent combinatorial synthetic methodology, which is illustrated by the solid-phase synthesis of a series of [3.3.0]-bicyclo [2,3]-Leu-enkephalin analogues. The reactions were optimized and the epimeric configurations were determined by 2D NMR spectroscopy. Biological assays show that these analogues have more potent δ binding affinity and bioactivity for δ vs μ opioid receptor, which may be related to the different conformations preferred by these analogues in our modeling studies.

Convenient Syntheses of Fluorenylmethyl-Based Side Chain Derivatives of Glutamic and Aspartic acids, Lysine and Cysteine

Efficient and practical one-pot syntheses of the fluorenylmethyl-based side chain derivatives of glutamic and aspartic acids, lysine, and cysteine are described.Likewise, stability/lability of these derivatives towards solvents and reagents used in solid