169825-97-2

Basic information

• Product Name: N-benzyloxycarbonyl-(2S,5S)-5-hydroxypipecolic acid tert-butyl ester
• Synonyms: N-benzyloxycarbonyl-(2S,5S)-5-hydroxypipecolic acid tert-butyl ester
• CAS NO: 169825-97-2
• Molecular Weight: 335.4
• Mol File: 169825-97-2.mol

Chemical Properties

• CAS DataBase Reference: N-benzyloxycarbonyl-(2S,5S)-5-hydroxypipecolic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzyloxycarbonyl-(2S,5S)-5-hydroxypipecolic acid tert-butyl ester(169825-97-2)
• EPA Substance Registry System: N-benzyloxycarbonyl-(2S,5S)-5-hydroxypipecolic acid tert-butyl ester(169825-97-2)

Safety Data

• Hazardous Substances Data: 169825-97-2(Hazardous Substances Data)

Upstream product

• 147489-30-3 (2S)-5-oxopiperidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester 
• 81470-51-1 tert-butyl N-benzyloxycarbonyl-L-pyroglutamate 

Downstream Products

• 1356384-03-6 N-Cbz-5-(S)-dibenzylphosphate-(S)-pipecolic acid 
• 1356384-01-4 N-Cbz-5-(S)-dibenzylphosphate-(S)-tert-butylpipecolate 
• 1452466-19-1 {2-[({[(2S,5R)-6-benzyloxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]ethyl}carbamic acid tert-butyl ester 
• 1452458-86-4 RG₆₀₈₀ 
• 1426573-07-0 (2S,5R)-1-[(1,1-dimethylethyl)carbonyl]-5-[(benzyloxy)amino]piperidine-2-carboxylic acid 
• 154307-84-3 (2S,5S)-5-hydroxypiperidine-2-carboxylic acid hydrogen chloride 
• 1452466-57-7 (2S,5R)-6-(benzyloxy)-N-methoxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide 
• 1452467-32-1 (2S,5R)-6-(benzyloxy)-7-oxo-N’-propanoyl-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide 
• 1426572-71-5 (2S,5R)-N’-acetyl-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide 
• 1383814-58-1 (2S,5R)-6-benzyloxy-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid methyl ester 
• 1416134-73-0 (2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxylate methyl ester 

Relevant articles and documents

NOVEL -LACTAMASE INHIBITOR AND METHOD FOR PRODUCING SAME

The currently available β-lactamase inhibitors are insufficient to inhibit the incessantly increasing β-lactamase, and novel β-lactamase inhibitors has been required today for the difficult treatment for bacterial infectious diseases caused by resistant bacteria which produce class C β-lactamase, extended-spectrum β-lactamase (ESBL) belonging to class A and D, or class A KPC-2 decomposing even carbapenem as a last resort for β-lactam antibiotic. A compound represented by the the formula (I), preparation process of the same, β-lactamase inhibitors and method for treating bacterial infectious diseases are provided.

OPTICALLY-ACTIVE DIAZABICYCLOOCTANE DERIVATIVE AND METHOD FOR MANUFACTURING SAME

Provided are an optically active diazabicyclooctane derivative defined by formula (F) below, which is useful as a pharmaceutical intermediate for β-lactamase inhibitor, and a process for preparing the same. In formula (F) above, R1 represents CO2R, CO2M, or CONH2, wherein R represents a methyl group, a tert-butyl group, an allyl group, a benzyl group, or a 2,5-dioxopyrrolidin-1-yl group, and M represents a hydrogen atom, an inorganic cation, or an organic cation; and R2 represents a benzyl group or an allyl group.

OPTICALLY ACTIVE DIAZABICYCLOOCTANE DERIVATIVES AND PROCESS FOR PREPARING THE SAME

Provided are an optically active diazabicyclooctane derivative defined by formula (F) below, which is useful as a pharmaceutical intermediate for beta-lactamase inhibitor, and a process for preparing the same. In formula (F) above, R1 represents CO2R, CO2M, or CONH2, wherein R represents a methyl group, a tert-butyl group, an allyl group, a benzyl group, or a 2,5-dioxopyrrolidin-1-yl group, and M represents a hydrogen atom, an inorganic cation, or an organic cation; and R2 represents a benzyl group or an allyl group.

Synthesis and evaluation of conformationally restricted inhibitors of aspartate semialdehyde dehydrogenase

Inhibitors of the enzyme aspartate semialdehyde dehydrogenase, a key biological target for the generation of a new class of antibiotic compounds, have been developed. To investigate improvements to binding within an inhibitor series, the lowering of the entropic barrier to binding through conformational restriction was investigated. A library of linear and cyclic substrate analogues was generated and computational docking used to aid in structure selection. The cyclic phosphonate inhibitor 18 was thus identified as complimentary to the enzyme active-site. Synthesis and in vitro inhibition assay revealed a K i of 3.8 mM against natural substrate, where the linear analogue of 18, compound 15, had previously shown no inhibitory activity. Two further inhibitors, phosphate analogue diastereoisomers 17a and 17b, were synthesised and also found to have low millimolar Ki values. As a result of the computational docking investigations, a novel substrate binding interaction was discovered: hydrogen bonding between the substrate (phosphate hydroxy-group as the hydrogen bond donor) and the NADPH cofactor (2′-oxygen as the hydrogen bond acceptor). The Royal Society of Chemistry 2011.

Diastereoselective synthesis of (2S,5S)- and (2S,5R)-N-benzyloxycarbonyl-5-hydroxypipecolic acids from trans-4-hydroxy-l-proline

An efficient diastereoselective synthesis of cis- and trans-5-hydroxy-(2S)-N-benzyloxycarbonyl pipecolic acids, starting from trans-4-hydroxy-l-proline is described. The key synthetic strategies involve the regioisomeric ring expansion of keto ester 8 and diastereoselective reduction of ketone 11 in high selectivity and yield.