71336-69-1

Basic information

• Product Name: (+/-)-trans-ethyl 1-benzyl-4-hydroxy-5-oxopyrrolidine-3-carboxylate
• CAS NO: 71336-69-1
• Molecular Weight: 263.293
• Mol File: 71336-69-1.mol

Chemical Properties

• CAS DataBase Reference: (+/-)-trans-ethyl 1-benzyl-4-hydroxy-5-oxopyrrolidine-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-trans-ethyl 1-benzyl-4-hydroxy-5-oxopyrrolidine-3-carboxylate(71336-69-1)
• EPA Substance Registry System: (+/-)-trans-ethyl 1-benzyl-4-hydroxy-5-oxopyrrolidine-3-carboxylate(71336-69-1)

Safety Data

• Hazardous Substances Data: 71336-69-1(Hazardous Substances Data)

Upstream product

• 50-00-0 formaldehyd 
• 622-30-0 N-benzyl hydroxylalmine 
• 1520-50-9 but-2-enedioic acid diethyl ester 
• 103-49-1 dibenzylamine 
• 29601-98-7 N-benzylhydroxylamine hydrochloride 
• 3376-26-9 N-Benzylidenebenzylamine N-oxide 

Downstream Products

• 871086-00-9 (3S,4R)-1-benzyl-4-hydroxy-5-oxopyrrolidine-3-carboxylic acid 
• 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 
• 653592-04-2 (3R,4S)-1-((4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl)-4-((methylthio)methyl)pyrrolidin-3-ol 
• 849935-87-1 (3S,4S)-N-tert-butoxycarbonyl-3-hydroxy-4-hydroxymethylpyrrolidine 
• 849935-80-4 (3S,4S)-1-benzyl-4-(hydroxymethyl)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.

Development of a practical synthesis of a purine nucleoside phosphorylase inhibitor: BCX-4208

A practical synthesis of the purine nucleoside phosphorylase (PNP) inhibitor BCX-4208 (1) was accomplished in three telescoped steps. Mannich condensation of the 4-benzyloxy-9-deazahypoxanthine with (3R,4R)-3-hydroxy-4- (hydroxymethyl)pyrrolidine and formaldehyde followed by removal of the protecting group and crystallization furnished the desired product as a hydrochloride salt in 85% overall yield and 99.8% purity. A scalable synthesis of 9-deazahypoxanthine is also reported. 2009 American Chemical Society.

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.

IMPROVED METHOD FOR PREPARING 3-HYDROXY-4-HYDROXYMETHYL-PYRROLIDINE COMPOUNDS

A process for preparing (3R,4R)-3-hydroxy-4-hydroxymethylpyrrolidine, the compound of formula (I), or (3S,4S)-3-hydroxy-4-hydroxymethylpyrrolidine, the compound of formula (Ia) involving, as a key step, the enzyme-catalysed enantioselective hydrolysis of a racemic 3,4-trans-disubstituted pyrrolidinone compound of formula (II).