71405-00-0

Upstream product

• 3262-72-4 (S)-N-(tert-butoxycarbonyl)serine 
• 2687-43-6 O-benzylhydoxylamine hydrochloride 
• 71404-98-3 (R)-2-((tert-butoxycarbonyl)amino)-3-chloropropanoic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 71605-42-0 O-benzyl-N-t-BOC-β-chloro-L-alanine hydroxamate 
• 622-33-3 N-benzyloxyamine 

Downstream Products

• 210547-97-0 (S)-3-Benzyloxyamino-2-tert-butoxycarbonylamino-propionic acid 
• 1260085-22-0 (S)-tert-butyl 1-(benzyloxy)-2-oxoazetidin-3-yl(methyl)carbamate 
• 129812-72-2 N^α-(tert-butoxycarbonyl)-N^β-<1-ethoxy-3-(6-carbobenzoxy-4-chloro-5-methylpyrimidin-2-yl)propion-3-yl>-(S)-β-aminoalanineamide 
• 129812-71-1 N^α-(tert-butoxycarbonyl)-N^β-<<(6-carbobenzoxy-4-chloro-5-methylpyrimidin-2-yl)methylene>amino>-(S)-β-aminoalanineamide 
• 90472-72-3 benzyl-<1(S)-<(1-benzyl-2-oxo-3(S)-azetidinyl)carbamoyl>butyl>-carbamate 

Relevant academic research and scientific papers

In Silico Design and Enantioselective Synthesis of Functionalized Monocyclic 3-Amino-1-carboxymethyl-β-lactams as Inhibitors of Penicillin-Binding Proteins of Resistant Bacteria

As a complement to the renowned bicyclic β-lactam antibiotics, monocyclic analogues provide a breath of fresh air in the battle against resistant bacteria. In that framework, the present study discloses the in silico design and unprecedented ten-step synthesis of eleven nocardicin-like enantiomerically pure 2-{3-[2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-2-oxoazetidin-1-yl}acetic acids starting from serine as a readily accessible precursor. The capability of this novel class of monocyclic 3-amino-β-lactams to inhibit penicillin-binding proteins (PBPs) of various (resistant) bacteria was assessed, revealing the potential of α-benzylidenecarboxylates as interesting leads in the pursuit of novel PBP inhibitors. No deactivation by representative enzymes belonging to the four β-lactamase classes was observed, while weak inhibition of class C β-lactamase P99 was demonstrated.

Total synthesis of mycobactin analogues as potent antimycobacterial agents using a minimal protecting group strategy

Mycobactins are a family of iron sequestering agents (siderophores) biosynthesized as growth promoters by mycobacteria including Mycobacterium tuberculosis. They are important siderophors with high affinity and specificity for Fe(III) due to the chemical nature of their component chelating functional groups. The parent compounds and their synthetic analogues can be used for studies of natural iron uptake mechanisms. It was hypothesized by Snow and co-workers that alternate and modified mycobactin analogues might serve as antagonists of mycobacterial growth and be of important therapeutic value. Efficient syntheses of four different analogues are presented. Dramatic improvements on formation of amide and ester bonds were achieved using water soluble carbodiimide (EDC-HCl)-mediated couplings in the presence of 1-hydroxy-7-azabenzotriazole (HOAt) as an additive. Using HOAt over other traditional coupling additives provided significant enhancement of the reaction rate of the desired coupling reactions and minimized side reactions. Further simplifications were made possible by minimizing the use of protecting groups during the syntheses. In fact, coupling components in the presence of free hydroxamic acids and a free phenolic hydroxyl group proceeded in excellent yields. Biological studies indicated that the resulting synthetic analogues effect moderate to high inhibition of the growth of M. tuberculosis H37Rv.

Synthesis of (S,S)-3-prolylazetidin-2-one: A key component in the synthesis of an HIV gp120 constrained immunogen

The title compound (2) was synthesized in 5 steps from D-serine. In the absence of protection of the carboxyl group, the β-lactam nucleus underwent a facile rearrangement to provide the undesired diazabicyclo[4.3.0]nonane compound, under acidic or basic c

Titanium Trichloride Reduction of Substituted N-Hydroxy-2-azetidinones and Other Hydroxamic Acids

A mild method of reduction of the N-O bond of substituted N-hydroxy-2-azetidinones was required to complete a hydroxamic acid mediated synthesis of substituted β-lactams.Of the several reduction methods studied, most either failed to reduce the N-O bond, cleaved the 2-azetidinone ring, or were inefficient and inconvenient.However, buffered titanium trichloride cleanly reduced the N-O bond of the N-hydroxy-2-azetidinones under conditions compatible with a peripheral acid-sensitive tert-butoxycarbonyl (Boc) group and the base-sensitive chiral center at C3.These results therefore constitute an efficient synthesis of β-lactams from substituted serinehydroxamic acids.The competitive C-O and N-O reductions of noncyclic hydroxamic acids of various substitution patterns are also described.