26048-92-0

Usage

Chemical Properties

White Solid

InChI:InChI=1/C15H22N2O5/c1-15(2,3)22-14(20)16-12(9-18)13(19)17-21-10-11-7-5-4-6-8-11/h4-8,12,18H,9-10H2,1-3H3,(H,16,20)(H,17,19)/t12-/m0/s1

Upstream product

• 2766-43-0 N-tert-butyloxycarbonyl-L-serine methyl ester 
• 2687-43-6 O-benzylhydoxylamine hydrochloride 
• 3262-72-4 (S)-N-(tert-butoxycarbonyl)serine 

Downstream Products

• 154617-89-7 O⁴-Benzyl-N-(tert-butyloxycarbonyl)neoenactin A 
• 26191-98-0 L-serine O-benzylhydroxamate N-hydrochloride 
• 71405-01-1 3-<(tert-butoxycarbonyl)amino>-1-hydroxy-2-azetidinone 
• 210547-99-2 [(S)-1-[(S)-1-(tert-Butyl-diphenyl-silanyloxy)-2-oxo-azepan-3-ylcarbamoyl]-2-((S)-6-(hexadecanoyl-hydroxy-amino)-2-{[(S)-2-(2-hydroxy-phenyl)-4,5-dihydro-oxazole-4-carbonyl]-amino}-hexanoylamino)-ethyl]-carbamic acid tert-butyl ester 
• 210547-98-1 {(S)-2-Benzyloxyamino-1-[(S)-1-(tert-butyl-diphenyl-silanyloxy)-2-oxo-azepan-3-ylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester 

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.

One-step synthesis of O-benzyl hydroxamates from unactivated aliphatic and aromatic esters

We have developed a simple and high yielding one-step method for the synthesis of hydroxamate derivatives directly from a broad range of unactivated esters and the anion of O-benzyl-hydroxylamine generated in situ. The reaction takes place in minutes at -

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.