177587-81-4

Upstream product

• 7541-17-5 tert-butyl N,N-dimethylcarbamate 
• 598-30-1 sec.-butyllithium 
• 75844-69-8 t-butyl piperidinecarboxylate 
• 86953-79-9 tert-butyl pyrrolidine-1-carboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 110-70-3 N,N`-dimethylethylenediamine 

Downstream Products

• 560101-02-2 (2-{[hydroxy-(4-hydroxy-phenyl)-acetyl]-methyl-amino}-ethyl)-methyl-carbamic acid tert-butyl ester 
• 560101-08-8 carbonic acid {[2-(tert-butoxycarbonyl-methyl-amino)-ethyl]-methyl-carbamoyl}-[4-({2-[(3-hydroxy-3-methyl-5-oxo-hexyloxycarbonyl)-methyl-amino]-ethyl}-methyl-carbamoyloxy)-phenyl]-methyl ester 4-nitro-phenyl ester 
• 560101-06-6 (2-{[4-({[2-(tert-butoxycarbonyl-methyl-amino)-ethyl]-methyl-carbamoyl}-hydroxy-methyl)-phenoxycarbonyl]-methyl-amino}-ethyl)-methyl-carbamic acid 3-hydroxy-3-methyl-5-oxo-hexyl ester 
• 560101-04-4 carbonic acid 4-({[2-(tert-butoxycarbonyl-methyl-amino)-ethyl]-methyl-carbamoyl}-hydroxy-methyl)-phenyl ester 4-nitro-phenyl ester 

Relevant academic research and scientific papers

An efficient methodology to introduce o-(aminomethyl)phenyl-boronic acids into peptides: alkylation of secondary amines

Current approaches for incorporating boronic acids into peptides require one of the following: the synthesis of commercially unavailable pinacol-protected boronate ester amino acid building blocks, amidation of small-molecule amine-containing boronic acids, or reductive amination of amine residues with 2-formylphenyl boronic acid. These methods have drawbacks, such as the use of excess starting materials, the lack of reactive-site specificity, or the inability to add multiple boronic acids in solution. In addition, several of these approaches do not allow for incorporation of the critical o-aminomethyl functionality that allows for binding of saccharides under physiological conditions. In this work, we report three methods to functionalize synthetic peptides with boronic acids using solid-phase and solution-phase chemistries by alkylating a secondary amine with o-(bromomethyl)phenylboronic acid. Solution-phase chemistries afforded the highest yields, and were used to synthesize seven complex biotinylated multi-boronic acid peptides.

CHEMICAL COMPOUNDS

The present invention provides novel compounds that demonstrate protective effects on target cells from HIV infection in a manner as to bind specifically to the chemokine receptor, and which affect the binding of the natural ligand or chemokine to a receptor such as CXCR4 and/or CCR5 of a target cell.

Halogen- and N-Haloimide-Promoted Homo- and Heterocoupling of α-(N-Carbamoyl)alkylcuprates and α-(Alkoxy)alkylcuprates

Both homo- and mixed lithium di-α-(heteroatom)alkylcuprates readily dimerize upon addition of halogens (e.g., I2, Br2) or N-halosuccinimides to afford the coupled products in excellent yields. Higher yields result when the requisite α-(heteroatom)alkyllithium reagents are generated via deprotonation rather than by transmetalation of the corresponding stannanes. Mixed lithium dialkyl- or alkyl-(aryl)cuprate reagents containing one α-(heteroatom)alkyl ligand and one simple alkyl or aryl ligand give significantly lower yields of coupled product. Low enantioselectivity has been achieved in the oxidative coupling of lithium (n-Bu)-(2-pyrrolidinyl)cuprate.