64187-48-0

Basic information

• Product Name: Z-HYP-OME
• Synonyms: N-Cbz-trans-4-hydroxy-L-proline methyl ester;Z-O-tert-Butyl-L-4-hydroxyproline;(2S,4R)-1-(Benzyloxycarbonyl)-2-(methoxycarbonyl)-4-hydroxypyrrolidine;(2S,4R)-1-Benzyloxycarbonyl-4-hydroxypyrrolidin-2-carboxylic acid methyl ester;1-Benzyl 2-methyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate;N-(Benzyloxycarbonyl)-4-hydroxyproline methyl ester;(2S,4R)-1-benzyl 2-Methyl 4-hydro×ypyrrolidine-1,2-dicarbo×ylate;N-Benzyloxycarbonyl-4-trans-hydroxy-L-proline Methyl ester, 98%
• CAS NO: 64187-48-0
• Molecular Formula: C₁₄H₁₇NO₅
• Molecular Weight: 279.29
• EINECS: 236-831-2
• Mol File: 64187-48-0.mol
• Article Data: 62

Chemical Properties

• Boiling Point: 422.779 °C at 760 mmHg
• Flash Point: 209.49 °C
• Appearance: Pale yellow/viscous liquid
• Density: 1.313
• Vapor Pressure: 6.67E-08mmHg at 25°C
• Refractive Index: 1.572
• Storage Temp.: −20°C
• PKA: 14.25±0.40(Predicted)
• CAS DataBase Reference: Z-HYP-OME(CAS DataBase Reference)
• NIST Chemistry Reference: Z-HYP-OME(64187-48-0)
• EPA Substance Registry System: Z-HYP-OME(64187-48-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 64187-48-0(Hazardous Substances Data)

Usage

Description

Z-HYP-OME, also known as N-(Benzyloxycarbonyl)-4-hydroxyproline Methyl Ester, is a chemical compound that serves as an intermediate in the synthesis of various pharmaceutical and biologically active compounds. It plays a crucial role in the development of new drugs and therapies.

Uses

Used in Pharmaceutical Industry:
Z-HYP-OME is used as an intermediate in the synthesis of various pharmaceutical compounds for its ability to facilitate the creation of new drugs and therapies.
Used in Antibacterial Applications:
Z-HYP-OME is used in the synthesis of Doripenem (D534800), an antibacterial agent, for its contribution to the development of effective treatments against bacterial infections.

InChI:InChI=1/C14H17NO5/c1-19-13(17)12-7-11(16)8-15(12)14(18)20-9-10-5-3-2-4-6-10/h2-6,11-12,16H,7-9H2,1H3/t11-,12+/m1/s1

Upstream product

• 62210-73-5 N-<<(benzyloxy)carbonyl>oxy>-5-norbornene-2,3-dicarboximide 
• 1499-56-5 (R)-4-hydroxy-L-proline ethyl ester 
• 124-41-4 sodium methylate 
• 13500-53-3 N-benzyloxycarbonyl-(2S,4R)-4-hydroxyproline benzyl ester 
• 186581-53-3 diazomethane 
• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 67-56-1 methanol 
• 501-53-1 benzyl chloroformate 
• 74-88-4 methyl iodide 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 
• 16217-15-5 1-benzyloxycarbonyl-4-oxo-L-proline methyl ester 
• 51-35-4 4R-4-hydroxyproline 
• 64187-47-9 1-benzyloxycarbonyl-4-keto-L-proline 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 

Downstream Products

• 122350-62-3 (2S,4R)-4-((2R,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 
• 122350-62-3 (2S,4R)-4-((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 

Relevant articles and documents

Synthesis of γ-Hydroxy-α-amino Acid Derivatives by Enzymatic Tandem Aldol Addition-Transamination Reactions

Three enzymatic routes toward γ-hydroxy-α-amino acids by tandem aldol addition-transamination one-pot two-step reactions are reported. The approaches feature an enantioselective aldol addition of pyruvate to various nonaromatic aldehydes catalyzed by trans-o-hydroxybenzylidene pyruvate hydratase-aldolase (HBPA) from Pseudomonas putida. This affords chiral 4-hydroxy-2-oxo acids, which were subsequently enantioselectively aminated using S-selective transaminases. Three transamination processes were investigated involving different amine donors and transaminases: (i) l-Ala as an amine donor with pyruvate recycling, (ii) a benzylamine donor using benzaldehyde lyase from Pseudomonas fluorescens Biovar I (BAL) to transform the benzaldehyde formed into benzoin, minimizing equilibrium limitations, and (iii) l-Glu as an amine donor with a double cascade comprising branched-chain α-amino acid aminotransferase (BCAT) and aspartate amino transferase (AspAT), both from E. coli, using l-Asp as a substrate to regenerate l-Glu. The γ-hydroxy-α-amino acids thus obtained were transformed into chiral α-amino-γ-butyrolactones, structural motifs found in many biologically active compounds and valuable intermediates for the synthesis of pharmaceutical agents.

MACROCYCLIC RIP2-KINASE INHIBITORS

The present invention relates to macrocyclic compounds and compositions containing said compounds acting as kinase inhibitors, in particular as inhibitors of RIP2-kinase, and/or mutants thereof, for use in the diagnosis, prevention and/or treatment of RIP2-kinase associated diseases. Moreover, the present invention provides methods of using said compounds, for instance as a medicine or diagnostic agent.

Practical Gram-Scale Synthesis of Iboxamycin, a Potent Antibiotic Candidate

A gram-scale synthesis of iboxamycin, an antibiotic candidate bearing a fused bicyclic amino acid residue, is presented. A pivotal transformation in the route involves an intramolecular hydrosilylation-oxidation sequence to set the ring-fusion stereocenters of the bicyclic scaffold. Other notable features of the synthesis include a high-yielding, highly diastereoselective alkylation of a pseudoephenamine amide, a convergent sp3-sp2 Negishi coupling, and a one-pot transacetalization-reduction reaction to form the target compound's oxepane ring. Implementation of this synthetic strategy has provided ample quantities of iboxamycin to allow for its in vivo profiling in murine models of infection.