871086-00-9

Basic information

• Product Name: (3S,4R)-1-benzyl-4-hydroxy-5- oxopyrrolidine-3-carboxylic acid
• Synonyms: (3S,4R)-1-benzyl-4-hydroxy-5- oxopyrrolidine-3-carboxylic acid
• CAS NO: 871086-00-9
• Molecular Formula: C₁₂H₁₃NO₄
• Molecular Weight: 235.23592
• EINECS: -0
• Mol File: 871086-00-9.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3S,4R)-1-benzyl-4-hydroxy-5- oxopyrrolidine-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4R)-1-benzyl-4-hydroxy-5- oxopyrrolidine-3-carboxylic acid(871086-00-9)
• EPA Substance Registry System: (3S,4R)-1-benzyl-4-hydroxy-5- oxopyrrolidine-3-carboxylic acid(871086-00-9)

Safety Data

• Hazardous Substances Data: 871086-00-9(Hazardous Substances Data)

Usage

General Description

The chemical (3S,4R)-1-benzyl-4-hydroxy-5-oxopyrrolidine-3-carboxylic acid is a compound with a molecular formula of C15H17NO4. It is a derivative of pyrrolidine-3-carboxylic acid and contains a benzyl group and a hydroxy group. (3S,4R)-1-benzyl-4-hydroxy-5- oxopyrrolidine-3-carboxylic acid has potential applications in pharmaceutical and medicinal chemistry due to its structural features and potential biological activities. The exact properties and uses of this chemical may vary depending on its specific application, but it is likely to be studied for its potential therapeutic effects or as a building block for the synthesis of other compounds.

Upstream product

• 71336-69-1 (+/-)-trans-ethyl 1-benzyl-4-hydroxy-5-oxopyrrolidine-3-carboxylate 
• 3376-26-9 N-Benzylidenebenzylamine N-oxide 
• 29601-98-7 N-benzylhydroxylamine hydrochloride 
• 103-49-1 dibenzylamine 
• 622-30-0 N-benzyl hydroxylalmine 

Downstream Products

• 253129-03-2 (3R, 4R)-1-benzyl-4-(hydroxymethyl)pyrrolidin-3-ol 
• 502485-10-1 C₄₁H₃₉NO₆ 
• 267421-93-2 (3R,4R)-3-hydroxy-4-(hydroxymethyl)pyrrolidine 
• 362600-15-5 N-Fmoc-(3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol 
• 635319-09-4 tert-butyl (3R,4R)-3-hydroxy-4-(hydroxymethyl)pyrrolidine-1-carboxylate 
• 666831-24-9 tert-butyl (3R,4R)-3-hydroxy-4-[(methanesulfonyloxy)methyl]pyrrolidine-1-carboxylate 
• 666831-26-1 (3R,4S)-tert-butyl 3-hydroxy-4-((methylthio)methyl)pyrrolidine-1-carboxylate 
• 653592-04-2 (3R,4S)-1-((4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl)-4-((methylthio)methyl)pyrrolidin-3-ol 

Relevant articles and documents

COMPOSITIONS AND METHODS FOR THERAPY OF PROSTATE CANCER USING DRUG COMBINATIONS TO TARGET POLYAMINE BIOSYNTHESIS AND RELATED PATHWAYS

Provided are compositions and methods for treating prostate conditions. The methods involve administering to an individual in need thereof a composition that contains i) an inhibitor of methionine salvage pathway in prostate of the individual and ii) a polyamine analogue. The methods are for use in individuals who have been diagnosed with, or are suspected of having or at risk for developing androgen sensitive prostate cancer (AS-CaP), or Castration recurrent CaP (CR-CaP), or benign prostate hyperplasia (BPH). The disclosure includes use of inhibitors of methylthioadenosine phosphorylase (MTAP), and a polyamine analog that upregulates polyamine catabolism by increasing spermidine/spermine Nl -acetyl transferase (SAT1) activity, such as methylthio-DADMe-Immucillin (MTDIA), andl),N(11)-bisethylnorspermine (BENSpm), respectively. Pharmaceutical formulations that contain a combination of the inhibitor of the methionine salvage pathway and a polyamine analogue are included, as are kits that contain such agents.

Profiling base excision repair glycosylases with synthesized transition state analogs

Two base excision repair glycosylase (BER) transition state (TS) mimics, (3R,4R)-1-benzyl (hydroxymethyl) pyrrolidin-3-ol (1NBn) and (3R,4R)- (hydroxymethyl) pyrrolidin-3-ol (1N), were synthesized using an improved method. Several BER glycosylases that repair oxidized DNA bases, bacterial formamidopyrimdine glycosylase (Fpg), human OG glycosylase (hOGG1) and human Nei-like glycosylase 1 (hNEIL1) exhibit exceptionally high affinity (K d～pM) with DNA duplexes containing the 1NBn and 1N nucleotide. Notably, comparison of the Kd values of both TS mimics relative to an abasic analog (THF) in duplex contexts paired opposite C or A suggest that these DNA repair enzymes use distinctly different mechanisms for damaged base recognition and catalysis despite having overlapping substrate specificities.

A practical synthesis of (3R,4R)-N-tert-butoxycarbonyl-4- hydroxymethylpyrrolidin-3-ol

The title compound (+)-5, required for production of transition state analogue inhibitors of enzymes involved in T-cell-dependent disorders, was synthesized in five steps. A 1,3-dipolar cycloaddition of the nitrone formed from formaldehyde and N-benzylhydroxylamine to diethyl maleate gave the racemic cis-isoxazolidine (±)-7. Reduction of the N-O bond of this compound gave pyrrolidone (±)-8 in excellent yield. A very efficient enzymic resolution of this racemic product led to the title enantiomer (+)-5. This route employs only one chromatographic purification. The Royal Society of Chemistry.