26048-92-0

Basic information

• Product Name: N-BOC-L-SER-NHOBN
• Synonyms: N-BOC-L-SER-NHOBN;[(1S)-1-(Hydroxymethyl)-2-oxo-2-[(phenylmethoxy)amino]ethyl]carbamic Acid 1,1-Dimethylethyl Ester;L-[1-[(Benzyloxy)carbamoyl]-2-hydroxyethyl]carbamic Acid tert-Butyl Ester;NSC 337388;O-Benzyl-α-N-tert-Boc-L-serinehydroxamic Acid;O-Benzyl-a-N-tert-Boc-L-serinehydroxamic Acid
• CAS NO: 26048-92-0
• Molecular Formula: C₁₅H₂₂N₂O₅
• Molecular Weight: 310.35
• Product Categories: pharmacetical;Amino Acids 13C, 2H, 15N;Amino Acids & Derivatives;Aromatics
• Mol File: 26048-92-0.mol
• Article Data: 3

Chemical Properties

• Appearance: White Solid
• Density: 1.192 g/cm³
• Refractive Index: 1.53
• Solubility: Chloroform, Dichloromethane, Methanol
• CAS DataBase Reference: N-BOC-L-SER-NHOBN(CAS DataBase Reference)
• NIST Chemistry Reference: N-BOC-L-SER-NHOBN(26048-92-0)
• EPA Substance Registry System: N-BOC-L-SER-NHOBN(26048-92-0)

Safety Data

• Hazardous Substances Data: 26048-92-0(Hazardous Substances Data)

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

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

Downstream Products

• 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 
• 370102-95-7 {(S)-2-Amino-1-[(S)-1-(tert-butyl-diphenyl-silanyloxy)-2-oxo-azepan-3-ylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester 
• 210547-97-0 (S)-3-Benzyloxyamino-2-tert-butoxycarbonylamino-propionic acid 

Relevant articles and documents

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.

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.