135042-17-0

Basic information

• Product Name: N-BOC-TRANS-4-HYDROXY-D-PROLINE METHYL ESTER
• Synonyms: N-BOC-TRANS-4-HYDROXY-D-PROLINE METHYL ESTER;(2R,4S)-1-tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate;(2R,4S)-4-hydroxypyrrolidine-1,2-dicarboxylate;(2R,4S)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-Methyl ester (N-Boc-trans-4-Hydroxy-D-proline Methyl ester;1,2-Pyrrolidinedicarboxylic acid, 4-hydroxy-, 1-(1,1-diMethylethyl) 2-Methyl ester, (2R,4S)-;Boc-trans-4-Hydroxy-D-proline Methyl ester;N-tert-butoxycarbonyl-trans-4-hydroxy-D-proline Methyl ester;(2R,4S)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester
• CAS NO: 135042-17-0
• Molecular Formula: C₁₁H₁₉NO₅
• Molecular Weight: 245.28
• EINECS: 1592732-453-0
• Mol File: 135042-17-0.mol

Chemical Properties

• Boiling Point: 335.244 °C at 760 mmHg
• Flash Point: 156.55 °C
• Appearance: /
• Density: 1.216±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 8.47E-06mmHg at 25°C
• Refractive Index: 1.5
• Storage Temp.: 2-8°C
• PKA: 14.27±0.40(Predicted)
• CAS DataBase Reference: N-BOC-TRANS-4-HYDROXY-D-PROLINE METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: N-BOC-TRANS-4-HYDROXY-D-PROLINE METHYL ESTER(135042-17-0)
• EPA Substance Registry System: N-BOC-TRANS-4-HYDROXY-D-PROLINE METHYL ESTER(135042-17-0)

Safety Data

• Hazardous Substances Data: 135042-17-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
N-BOC-TRANS-4-HYDROXY-D-PROLINE METHYL ESTER is used as a building block in the synthesis of pharmaceutical compounds for its ability to be incorporated into peptide structures and other organic molecules, enhancing the development of new drugs with potential therapeutic benefits.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, N-BOC-TRANS-4-HYDROXY-D-PROLINE METHYL ESTER is used as a research tool to explore the properties and potential applications of novel compounds, contributing to the advancement of drug discovery and design.
Used in Organic Chemistry:
N-BOC-TRANS-4-HYDROXY-D-PROLINE METHYL ESTER is utilized as a reagent in organic chemistry for its versatility in forming various chemical bonds and structures, which can be crucial in the synthesis of complex organic molecules.
Used in Peptide Synthesis:
In peptide synthesis, N-BOC-TRANS-4-HYDROXY-D-PROLINE METHYL ESTER is used as a protected amino acid derivative to facilitate the stepwise assembly of peptide chains, with the Boc group ensuring selectivity and preventing side reactions during the process.
Used in Drug Development:
N-BOC-TRANS-4-HYDROXY-D-PROLINE METHYL ESTER is employed in drug development as a key component in the design and synthesis of new pharmaceutical entities, potentially leading to the discovery of innovative treatments and therapies.

InChI:InChI=1/C11H19NO5/c1-11(2,3)17-10(15)12-6-7(13)5-8(12)9(14)16-4/h7-8,13H,5-6H2,1-4H3/t7-,8+/m0/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 51-35-4 4R-4-hydroxyproline 
• 148017-37-2 (2S,4S)-1-t-butoxycarbonyl-4-formyloxy-2-methoxycarbonylpyrrolidine 
• 87691-27-8 N-tert-butoxycarbonyl-L-cis-4-hydroxyproline 
• 77-78-1 dimethyl sulfate 
• 135042-16-9 N-(tert-butoxycarbonyl)-trans-4-acetoxy-D-proline methyl ester 
• 67-56-1 methanol 
• 148017-31-6 N-tert-Butoxycarbonyl-trans-4-formyloxy-D-proline methyl ester 
• 481704-21-6 (2R,4S)-methyl 4-hydroxypyrrolidine-2-carboxylate hydrochloride 
• 178962-09-9 methyl (2R,4S)-4-hydroxypyrrolidine-2-carboxylate 
• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 74-88-4 methyl iodide 
• 77449-94-6 (2R,4R)-4-hydroxypyrrolidine-2-carboxylic acid hydrochloride 
• 3398-22-9 trans-4-hydroxyproline 

Downstream Products

• 211298-60-1 (2S,4R)-4-(Biphenyl-2-yloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 848475-26-3 (2S,4S)-4-(4-Cyano-benzyloxy)-pyrrolidine-2-carboxylic acid methyl ester 
• 433289-51-1 (2S,4S)-4-(4-Bromo-benzyloxy)-pyrrolidine-2-carboxylic acid methyl ester 
• 433289-53-3 (2S,4S)-4-(3-Bromo-benzyloxy)-pyrrolidine-2-carboxylic acid methyl ester 
• 433289-48-6 (2S,4S)-4-(4-Bromo-phenoxy)-pyrrolidine-2-carboxylic acid methyl ester 
• 121148-00-3 1-(1,1-dimethylethyl) 2-methyl (2S,4R)-4-amino-1,2-pyrrolidinedicarboxylate 
• 876953-56-9 (2S,4R)-2-[(S)-1-((S)-1-Methoxycarbonyl-2-phenyl-ethylcarbamoyl)-3-methyl-butylcarbamoyl]-4-methylsulfanyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 842136-17-8 (2S,4S)-4-(4-Chloro-benzyloxy)-2-methanesulfonyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 842136-15-6 (2S,4S)-2-azidomethyl-4-(4-chlorobenzyloxy)pyrrolidine-1-carboxylic acid tert-butyl ester 
• 842136-19-0 (2S,4S)-2-Aminomethyl-4-(4-chloro-benzyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 842136-13-4 (2S,4S)-4-(4-chlorobenzyloxy)-2-hydroxymethylpyrrolidine-1-carboxylic acid tert-butyl ester 
• 876953-58-1 N-(tert-butyloxycarbonyl)-trans-4-(methylthio)-L-proline 
• 203866-14-2 (2S,4R)-1-[(tert-butoxy)carbonyl]-4-fluoropyrrolidine-2-carboxylic acid 
• 886447-53-6 ethyl [4-[(4R)-fluoro-1-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl]-(2S)-pyrrolidinylcarbonyl]-1-piperazinyl]acetate 

Relevant articles and documents

Synthesis of tri- and tetrasaccharide glycosides of (4S)-4-hydroxy-d-proline relevant to the cell wall O-glycans of green alga Chlamydomonas reinhardtii

The synthesis of tri- and tetrasaccharide glycosides of (4S)-4-hydroxy-d-proline 1 and 2 with unusual glycan motifs has been achieved efficiently. The assembly of the synthetically challenging 1,2-cis linked arabino- and galactofuranoside frameworks withi

Multipodal insulin mimetics built on adamantane or proline scaffolds

Multi-orthogonal molecular scaffolds can be applied as core structures of bioactive compounds. Here, we prepared four tri-orthogonal scaffolds based on adamantane or proline skeletons. The scaffolds were used for the solid-phase synthesis of model insulin mimetics bearing two different peptides on the scaffolds. We found that adamantane-derived compounds bind to the insulin receptor more effectively (Kd value of 0.5 μM) than proline-derived compounds (Kd values of 15–38 μM) bearing the same peptides. Molecular dynamics simulations suggest that spacers between peptides and central scaffolds can provide greater flexibility that can contribute to increased binding affinity. Molecular modeling showed possible binding modes of mimetics to the insulin receptor. Our data show that the structure of the central scaffold and flexibility of attached peptides in this type of compound are important and that different scaffolds should be considered when designing peptide hormone mimetics.

Altering the sex pheromone cyclo(L-pro-l-pro) of the diatom seminavis robusta towards a chemical probe

As a major group of algae, diatoms are responsible for a substantial part of the primary production on the planet. Pennate diatoms have a predominantly benthic lifestyle and are the most species-rich diatom group, with members of the raphid clades being motile and generally having heterothallic sexual reproduction. It was recently shown that the model species Seminavis robusta uses multiple sexual cues during mating, including cyclo(L-Pro-L-Pro) as an attraction pheromone. Elaboration of the pheromone-detection system is a key aspect in elucidating pennate diatom life-cycle regulation that could yield novel fundamental insights into diatom speciation. This study reports the synthesis and bio-evaluation of seven novel pheromone analogs containing small structural alterations to the cyclo(L-Pro-L-Pro) pheromone. Toxicity, attraction, and interference assays were applied to assess their potential activity as a pheromone. Most of our analogs show a moderate-to-good bioactivity and low-to-no phytotoxicity. The pheromone activity of azide-and diazirine-containing analogs was unaffected and induced a similar mating behavior as the natural pheromone. These results demonstrate that the introduction of confined structural modifications can be used to develop a chemical probe based on the diazirine-and/or azide-containing analogs to study the pheromone-detection system of S. robusta.

Design, Synthesis, and Biochemical Evaluation of Alpha-Amanitin Derivatives Containing Analogs of the trans-Hydroxyproline Residue for Potential Use in Antibody-Drug Conjugates

Alpha-amanitin, an extremely toxic bicyclic octapeptide extracted from the death-cap mushroom, Amanita phalloides, is a highly selective allosteric inhibitor of RNA polymerase II. Following on growing interest in using this toxin as a payload in antibody-drug conjugates, herein we report the synthesis and biochemical evaluation of several new derivatives of this toxin to probe the role of the trans-hydroxyproline (Hyp), which is known to be critical for toxicity. This structure activity relationship (SAR) study represents the first of its kind to use various Hyp-analogs to alter the conformational and H-bonding properties of Hyp in amanitin.

SUBSTITUTED AMINO TRIAZOLES USEFUL AS CHITINASE INHIBITORS

Disclosed are amino triazole compounds of formula (I). These compounds are inhibitors of acidic mammalian chitinase and chitotriosidase. Also disclosed are methods of using the compounds to treat asthma reactions caused by allergens, as well as acute and chronic inflammatory diseases, autoimmune diseases, dental diseases, neurologic diseases, metabolic diseases, liver diseases, polycystic ovary syndrome, endometriosis, and cancer.

Synthesis process of N-BOC-cis-4-hydroxyproline methyl ester

The invention discloses a synthesis process of N-BOC-cis-4-hydroxyproline methyl ester. The synthesis process comprises the following steps: (1) adding raw materials including dichloromethane, 4-hydroxy-L-proline and DMAP into a 2 L reaction flask, stirring, slowly dropwise adding BOC anhydride into the reaction liquid, after dropwise adding, sampling, carrying out TLC, completely reacting the rawmaterials, adding water into the reaction liquid after treatment, stirring at a temperature of 20-30 DEG C, separating the liquid, drying an organic phase by using anhydrous sodium sulfate, and concentrating under reduced pressure to obtain a white solid product; and (2) taking the obtained product, adding tetrahydrofuran and DCC into a 5 L reaction flask, stirring at 20-30 DEG C to react for 1 hour, dropwise adding methanol into the reaction solution, keeping the temperature after dropwise adding, sampling, carrying out TLC until the reaction is complete, filtering the reaction solution, collecting the filtrate, concentrating under reduced pressure until no liquid flows out to obtain a white solid crude product, heating, collecting the filtrate, collecting a filter cake, and drying the filter cake to obtain a white solid. According to the invention, the product is prepared with high quality and high yield.

Substituted Quinazoline and Pyridopyrimidine Derivatives Useful as Anticancer Agents

Compounds of the general formula: processes for the preparation of these compounds, compositions containing these compounds, and the uses of these compounds.

As Aurora kinase inhibitor derivatives

The present invention relates to a substituted pyrazole derivative used for inhibiting Aurora kinase and represented by formula (I) or formula (Ia), or stereo isomers, geometric isomers, tautomers, nitrogen oxides, hydrates, solvates, metabolites, esters, pharmaceutically acceptable salts or prodrugs thereof, a medicinal composition containing the above compounds as active ingredients, and a use of the compounds and the medicinal composition in preparation of medicines for protecting, processing, treating or mitigating proliferative diseases of patients.

Synthesis and antibacterial activity of 6(R)- and 6(S)-fluoropenibruguieramine As: Fluorine as a probe for testing the powerfulness of memory of chirality (MOC)

The synthesis of 6(R)- and 6(S)- fluoropenibruguieramine As has been achieved, employing the elegant strategy developed by Kim and co-workers. Single diastereomers were formed via the key intramolecular aldol reaction, and both of the products were unambiguously confirmed by X-ray diffraction crystallography. This reaction shows that the fluorine amide effect could not compete with the memory of chirality (MOC) effect, thus further demonstrating the powerfulness of MOC effect in asymmetric synthesis. The biological testing carried out in this work indicates that the principal of antibacterial activity of the natural extract is probably not penibruguieramine A.

SUBSTITUTED AMINO TRIAZOLES USEFUL AS HUMAN CHITINASE INHIBITORS

Disclosed are amino triazole compounds substituted with a piperidinyl ring that is itself substituted with a heterocyclic ring. These compounds are inhibitors of acidic mammalian chitinase and chitotriosidase. Also disclosed are methods of using the compounds to treat asthma reactions caused by allergens, as well as acute and chronic inflammatory diseases, autoimmune diseases, dental diseases, neurologic diseases, metabolic diseases, liver diseases, polycystic ovary syndrome, endometriosis, and cancer.