267421-93-2

Basic information

• Product Name: (3R,4R)-4-hydroxy-3-PyrrolidineMethanol
• Synonyms: (3R,4R)-4-hydroxy-3-PyrrolidineMethanol
• CAS NO: 267421-93-2
• Molecular Formula: C₅H₁₁NO₂
• Molecular Weight: 117.14634
• Mol File: 267421-93-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3R,4R)-4-hydroxy-3-PyrrolidineMethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4R)-4-hydroxy-3-PyrrolidineMethanol(267421-93-2)
• EPA Substance Registry System: (3R,4R)-4-hydroxy-3-PyrrolidineMethanol(267421-93-2)

Safety Data

• Hazardous Substances Data: 267421-93-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(3R,4R)-4-hydroxy-3-PyrrolidineMethanol is utilized as a key intermediate in organic synthesis for the production of various complex organic molecules. Its unique structure and chirality allow for the creation of enantiomerically pure compounds, which are essential in many chemical reactions and pharmaceutical development processes.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (3R,4R)-4-hydroxy-3-PyrrolidineMethanol is employed as a building block for the development of novel drugs. Its chiral nature and functional groups enable the design of molecules with specific biological activities, targeting various therapeutic areas such as central nervous system disorders, cardiovascular diseases, and oncology.
Used in Chiral Catalysts:
(3R,4R)-4-hydroxy-3-PyrrolidineMethanol can be used as a chiral catalyst in asymmetric synthesis, a technique crucial for producing enantiomerically pure compounds. Its presence can induce selectivity in chemical reactions, leading to the formation of desired enantiomers with high yields and selectivity, which is particularly important in the synthesis of pharmaceuticals and agrochemicals.
Used in Analytical Chemistry:
(3R,4R)-4-hydroxy-3-PyrrolidineMethanol can also be employed in analytical chemistry as a chiral derivatizing agent for the resolution and analysis of enantiomers. Its ability to selectively react with specific enantiomers allows for the separation and identification of chiral compounds in complex mixtures, which is vital in quality control and purity assessment of pharmaceutical products.

Upstream product

• 775577-31-6 Acetic acid (3R,4R)-4-acetoxymethyl-pyrrolidin-3-yl ester 
• 71336-69-1 (+/-)-trans-ethyl 1-benzyl-4-hydroxy-5-oxopyrrolidine-3-carboxylate 
• 871086-00-9 (3S,4R)-1-benzyl-4-hydroxy-5-oxopyrrolidine-3-carboxylic acid 
• 635319-09-4 tert-butyl (3R,4R)-3-hydroxy-4-(hydroxymethyl)pyrrolidine-1-carboxylate 
• 604798-42-7 (3R,4R)-(1-benzyl-4-benzyloxypyrrolidin-3-yl)methanol 
• 362600-14-4 N-Fmoc-(3R,4S)-4-[(1S)-1,2-dihydroxyethyl]pyrrolidin-3-ol 
• 807626-30-8 (3R,4R,1'S)-3-tert-butyldimethylsilyloxy-4-tert-butyldimethylsilyloxymethyl-1-(1'-phenylethyl)pyrrolidin-2-one 
• 807626-25-1 (3R,4R,1'S)-3-tert-butyldimethylsilyloxy-4-methoxycarbonyl-1-(1'-phenylethyl)pyrrolidin-2-one 
• 807626-26-2 (3S,4S,1'S)-3-tert-butyldimethylsilyloxy-4-methoxycarbonyl-1-(1'-phenylethyl)pyrrolidin-2-one 
• 807626-32-0 (3S,4R,1'S)-3-tert-butyldimethylsilyloxy-4-hydroxymethyl-1-(1'-phenylethyl)pyrrolidin-2-one 
• 807626-27-3 (3R,4R,1'S)-3-tert-butyldimethylsilyloxy-4-hydroxymethyl-1-(1'-phenylethyl)pyrrolidin-2-one 
• 807626-34-2 (3R,4R,1'S)-4-benzyloxymethyl-3-hydroxy-1-(1'-phenylethyl)pyrrolidin-2-one 
• 807626-31-9 (3R,4R,1'S)-3-acetoxy-4-acetoxymethyl-1-(1'-phenylethyl)pyrrolidine 
• 807626-23-9 1-ethyl-4-methyl-2-tert-butyldimethylsilyloxy-3-methylenebutanedioate 

Downstream Products

• 1609403-89-5 (3R,4R)-3-hydroxy-4-(hydroxymethyl)pyrrolidine hydrochloride 
• 1182051-00-8 (4R)-1-(((4-benzyloxy)-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl)-4-(hydroxymethyl)pyrrolidin-3-ol 
• 362600-15-5 N-Fmoc-(3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol 
• 253129-03-2 (3R, 4R)-1-benzyl-4-(hydroxymethyl)pyrrolidin-3-ol 
• 502485-10-1 C₄₁H₃₉NO₆ 
• 653592-04-2 (3R,4S)-1-((4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl)-4-((methylthio)methyl)pyrrolidin-3-ol 
• 604798-43-8 [(3R,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidin-3-yl]methanol 
• 537693-43-9 N-(pyren-1-ylmethyl)-(3R,4R)-4-[(4,4'-dimethoxytriphenylmethoxy)methyl]pyrrolidin-3-ol 
• 635319-09-4 tert-butyl (3R,4R)-3-hydroxy-4-(hydroxymethyl)pyrrolidine-1-carboxylate 

Relevant articles and documents

FUSED QUADRACYCLIC COMPOUNDS, COMPOSITIONS AND USES THEREOF

Provided herein are substituted fused quadracyclic compounds useful as inhibitors of MK2. The invention further provides pharmaceutical compositions of the compounds of the invention. The invention also provides medical uses of substituted fused quadracyclic compounds.

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.

SALT AND POLYMORPHIC FORMS OF (3R,4S)-L-((4-AMINO-5H-PYRROLO[3,2-D]PYRIMIDIN-7-YL)METHYL)-4(METHYLTHIOMETHYL)PYRODIN-3-OL(MTDIA)

The invention relates to salt forms of (3R,4S)-1-((4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl)-4-(methylthiomethyl)pyrrolidin-3-ol, as well as polymorphic forms of the salts. The invention further relates to processes for preparing the salt forms and to the use of the salt forms in the treatment of diseases and disorders where it is desirable to inhibit 5'-methylthioadenosine phosphorylase (MTAP).

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.

Synthesis and antibacterial activity of novel pyrido[1,2,3-de][1,4] benzoxazine-6-carboxylic acid derivatives carrying the 3-cyclopropylaminomethyl- 4-substituted-1-pyrrolidinyl group as a C-10 substituent

Novel pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid derivatives 5-9 carrying a 3-cyclopropylami-nomethyl-4-substituted-1-pyrrolidinyl moiety at the C-10 position were synthesized and their in vitro antibacterial activity, intravenous single-dose toxi

DEAZAPURINE ANALOGS OF 1'-AZA-L-NUCLEOSIDES

The invention relates to compounds of the formula (I), which are L-enantiomeric forms of nucleoside analogues, and to pharmaceutical compositions containing the compounds, methods of treating certain diseases, including cancer, bacterial infection, parasitic infection, and T-cell mediated diseases, using the compounds, processes for preparing the compounds, and intermediates useful in the preparation of the compounds.

7-(4-SUBSTITUTED 3- CYCLOPROPYLAMINOMETHYL-1- PYRROLIDINYL) Q UINOLONECARBOXYLIC ACID DERIVATIVE

To provide novel quinolonecarboxylic acid compounds serving as safe, strong antibacterial agents that are effective against drug-resistant bacteria that are less susceptible to conventional antibacterial agents. SOLVING MEANS There are provided 7-(4-substituted-3-cyclopropylaminomethylpyrrolidinyl)quinolonecarboxylic acid derivatives (such as 1-cyclopropyl-7-[(3S,4S)-3-cyclopropylaminomethyl-4-fluoro-1-pyrrolidinyl]-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid) that exhibit strong antibacterial activity against gram-positive bacteria, such as MRSA, PRSP and VRE, while being safe. The compounds are shown by the following general formula (I):

Syntheses and bio-activities of the l-enantiomers of two potent transition state analogue inhibitors of purine nucleoside phosphorylases

(1R)-1-(9-Deazahypoxanthin-9-yl)-1,4-dideoxy-1,4-imino-l-ribitol [(+)-5] and (3S,4S)-1-[(9-deazahypoxanthin-9-yl)methyl]-4-(hydroxymethyl)pyrrolidin-3-ol [(-)-6] are the l-enantiomers of immucillin-H (d-ImmH) and DADMe-immucillin-H (d-DADMe-ImmH), respectively, these d-isomers being high affinity transition state analogue inhibitors of purine nucleoside phosphorylases (PNPases) developed as potential pharmaceuticals against diseases involving irregular activation of T-cells. The C-nucleoside hydrochloride d-ImmH [(-)-5)·HCl], now "Fodosine" is in phase II clinical trials as an anti-T-cell leukaemia agent, while d-DADMe-ImmH is a second generation inhibitor with extreme binding to the target enzyme and has entered the clinic for phase I testing as an anti-psoriasis drug. Since the enantiomers of some pharmaceuticals have revealed surprising biological activities, the l-nucleoside analogues (+)-5·HCl and (-)-6, respectively, of d-ImmH and d-DADMe-ImmH, were prepared and their PNPase binding properties were studied. For the synthesis of compound (-)-6 suitable enzyme-based routes to the enantiomerically pure starting material (3S,4S)-4-(hydroxymethyl)pyrrolidin-3-ol [(-)-16] and its enantiomer were developed. The l-enantiomers (+)-5·HCl and (-)-6 bind to the PNPases approximately 5- to 600-times less well than do the d-compounds, but nevertheless remain powerful inhibitors with nanomolar dissociation constants. The Royal Society of Chemistry 2006.

A practical large-scale synthesis of (3R,4R)-4-(Hydroxymethyl)pyrrolidin-3- ol via asymmetric 1,3-dipolar cycloaddition

(3R,4R)-4-(Hydroxymethyl)pyrrolidin-3-ol (1), which is a useful intermediate for the synthesis of various bioactive molecules, has been synthesized in 51% overall yield by 1,3-dipolar cycloaddition reaction from the dipolarophile, (E)-3-benzyloxypropenoyl-(2′S)-bornane-10,2-sultam (5), and the achiral ylide precursor, N-(benzyl)-N-(methoxymethyl)-N- (trimethylsilylmethyl)amine (6), without using chromatography and the subsequent reduction with LAH and catalytic hydrogenation. The diastereomers 7 and 8 were separated by crystallization, and efficient procedures were developed for the subsequent reactions to afford 1.