1009335-39-0

Basic information

• Product Name: (2R,4R)-benzyl 4-hydroxy-2-(hydroxyMethyl)pyrrolidine-1-carboxylate
• Synonyms: (2R,4R)-benzyl 4-hydroxy-2-(hydroxyMethyl)pyrrolidine-1-carboxylate;N-CBZ-cis-4-Hydroxy-L-prolinol
• CAS NO: 1009335-39-0
• Molecular Formula: C₁₃H₁₇NO₄
• Molecular Weight: 251.27838
• Mol File: 1009335-39-0.mol

Chemical Properties

• Boiling Point: 433.9±40.0 °C(Predicted)
• Appearance: /
• Density: 1.297±0.06 g/cm3(Predicted)
• PKA: 14.56±0.40(Predicted)
• CAS DataBase Reference: (2R,4R)-benzyl 4-hydroxy-2-(hydroxyMethyl)pyrrolidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,4R)-benzyl 4-hydroxy-2-(hydroxyMethyl)pyrrolidine-1-carboxylate(1009335-39-0)
• EPA Substance Registry System: (2R,4R)-benzyl 4-hydroxy-2-(hydroxyMethyl)pyrrolidine-1-carboxylate(1009335-39-0)

Safety Data

• Hazardous Substances Data: 1009335-39-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(2R,4R)-benzyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate is used as a chiral building block for the synthesis of enantiopure compounds, which are essential in the development of single-enantiomer drugs. Its chiral nature ensures that the synthesized compounds have specific biological activities and reduced side effects.
Used in Organic Synthesis:
(2R,4R)-benzyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate is used as a valuable intermediate in the synthesis of bioactive molecules. Its unique structure allows for the creation of a wide range of compounds with potential applications in various fields, such as medicine, agrochemistry, and materials science.
Used in Chiral Pool Synthesis:
(2R,4R)-benzyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate is used as a chiral pool compound for the asymmetric synthesis of complex organic molecules. Its readily available enantiomers and versatile functional groups make it an ideal candidate for the development of novel synthetic routes and the production of enantioselective catalysts.
Used in Drug Discovery:
(2R,4R)-benzyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate is used as a starting material in drug discovery programs, where its chiral properties can be exploited to design and synthesize new pharmaceutical agents with improved efficacy and selectivity. Its potential as a precursor for bioactive molecules makes it a valuable tool in the search for novel therapeutic agents.

Upstream product

• 2584-71-6 cis-hydroxy-D-proline 
• 501-53-1 benzyl chloroformate 
• 130930-25-5 (R,R)-4-hydroxy-1-(benzyloxycarbonyl)pyrrolidine-2-carboxylic acid 
• 155075-23-3 (2R,4R)-1-benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate 

Downstream Products

• 1009335-36-7 (3R,5R)-5-(hydroxymethyl)pyrrolidin-3-ol hydrochloride 
• 1448706-18-0 C₂₃H₂₅Cl₂N₃O₂S 
• 1448706-17-9 C₂₂H₂₃Cl₂N₃O₂S 
• 1256344-57-6 cis-4-hydroxy-(R)-Cbz-prolinal 

Relevant articles and documents

Structure guided design of a series of sphingosine kinase (SphK) inhibitors

Sphingosine-1-phosphate (S1P) signaling plays a vital role in mitogenesis, cell migration and angiogenesis. Sphingosine kinases (SphKs) catalyze a key step in sphingomyelin metabolism that leads to the production of S1P. There are two isoforms of SphK and observations made with SphK deficient mice show the two isoforms can compensate for each other's loss. Thus, inhibition of both isoforms is likely required to block SphK dependent angiogenesis. A structure based approach was used to design and synthesize a series of SphK inhibitors resulting in the identification of the first potent inhibitors of both isoforms of human SphK. Additionally, to our knowledge, this series of inhibitors contains the only sufficiently potent inhibitors of murine SphK1 with suitable physico-chemical properties to pharmacologically interrogate the role of SphK1 in rodent models and to reproduce the phenotype of SphK1 (-/-) mice.

Structure-guided minimalist redesign of the L-fuculose-1-phosphate aldolase active site: Expedient synthesis of novel polyhydroxylated pyrrolizidines and their inhibitory properties against glycosidases and intestinal disaccharidases

A minimalist active site redesign of the L-fuculose-1-phosphate aldolase from E. coli FucA was envisaged, to extend its tolerance towards bulky and conformationally restricted N-Cbz-amino aldehyde acceptor substrates (Cbz = benzyloxycarbonyl). Various mutants at the active site of the FucA wild type were obtained and screened with seven sterically demanding N-Cbz-amino aldehydes including N-Cbz-prolinal derivatives. FucA F131A showed an aldol activity of 62μmol-1mg-1 with (R)-N-Cbz-prolinal, whereas no detectable activity was observed with the FucA wild type. For the other substrates, the F131A mutant gave aldol activities from 4 to about 25 times higher than those observed with the FucA wild type. With regard to the stereochemistry of the reactions, the (R)-amino aldehydes gave exclusively the anti configured aldol adducts whereas their 5 counterparts gave variable ratios of anti/syn diastereoisomers. Interestingly, the F131A mutant was highly stereoselective both with (R)and with (S)-N-Cbz-prolinal, exclusively producing the anti and syn aldol adducts, respectively. Molecular models suggest that this improved activity towards bulky and more rigid substrates, such as N-Cbz-prolinal, could arise from a better fit of the substrate into the hydrophobic pocket created by the F131A mutation, due to an additional π-cation interaction with the residue K205' and to efficient contact between the substrate and the mechanistically important Y113' and Y209' residues. An expedient synthesis of novel polyhydroxylated pyrrolizidines related to the hyacinthacine and alexine types was accomplished through aldol additions of dihydroxyacetone phosphate (DHAP) to hydroxyprolinal derivatives with the hyperactive FucA F131A as catalyst. The iminocyclitols obtained were fully characterised and found to be moderate to weak inhibitors (relative to 1,4-dideoxy-1,4-imino-L-arabinitol (LAB) and 1,4-dideoxy-1,4-iminoD-arabinitol (DAB)) against glycosidases and rat intestinal saccharidases.

Prolinol-based nucleoside phosphonic acids: new isosteric conformationally flexible nucleotide analogues

trans-4-Hydroxy-l-proline has been used as a starting material for the synthesis of prolinol-based nucleotide analogues with an N-phosphonomethyl moiety attached to the prolinol ring nitrogen atom. The synthetic methodology based on the inversion of configuration at both 1- and 4-position led to all diastereoisomeric O-protected 4-mesyloxyprolinol-N-phosphonates. Alkylation of nucleobases using the synthons in the l-series afforded the nucleotide analogues corresponding to α-l- and β-l-nucleotide. The NMR-based conformational study of these compounds in aqueous solution performed at two different pH values, showing either N-fully protonated or deprotonated forms, revealed the occurrence of the same mostly populated conformer in both cases. All final l-prolinol-based nucleoside phosphonic acids were tested for cytotoxic and antiviral properties, but no significant activity was found.

AZA-BENZOFURANYL COMPOUNDS AND METHODS OF USE

The invention relates to azabenzofuranyl compounds of Formula (I) with anti-cancer and/or anti-inflammatory activity and more specifically to azabenzofuranyl compounds which inhibit MEK kinase activity. The invention provides compositions and methods useful for inhibiting abnormal cell growth or treating a hyperproliferative disorder, or treating an inflammatory disease in a mammal. The invention also relates to methods of using the compounds for in vitro, in situ, and in vivo diagnosis or treatment of mammalian cells, or associated pathological conditions.

Oligonucleotide analogues with 4-hydroxy-N-acetylprolinol as sugar substitute

Modified oligonucleotides incorporating trans-4-hydroxy-N-acetyl-L-prolinol (trans-4-HO-L-NAP) or its D-analogue as sugar substitute were synthesised with adenine and thymine as nucleobases. All-adenine oligonucleotides built from (2S,4S) or (2R,4R)-cis-4

Nucleosides and Oligonucleotides Derived from trans-4-Hydroxy-N-acetylprolinol

The 4-O-phosphoramidites of monomethoxytritylated 4-hydroxy-N-6-benzoyladenin-9-yl)acetyl>prolinol and 4-hydroxy-N-prolinol were prepared for incorporation into nucleic acids.The L-trans all-adenine oligonucleotide (ON) hybridises to natural oligothymidylate, apparently via triplex formation.All-purine sequences of the L-trans form can also form homo-complexes with their pyrimidine counterpart.The D-trans compounds give larger destabilisation when inserted in DNA.D-trans all-adenine ONs do not form complexes with natural oligothymidylate.For this series of modified ONs no hybridisation could be detected between complementary strands of opposite enantiomeric form.