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
• Article Data: 6

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

General Description

The chemical compound (2R,4R)-benzyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate is a derivative of pyrrolidine and is commonly used in organic chemistry as a chiral building block for the synthesis of pharmaceuticals and natural products. It contains a benzyl group, a hydroxymethyl group, and a carboxylate group attached to a pyrrolidine ring. (2R,4R)-benzyl 4-hydroxy-2-(hydroxyMethyl)pyrrolidine-1-carboxylate has potential applications in the pharmaceutical industry due to its chiral nature, which makes it useful in the synthesis of enantiopure compounds. It can also be used as a precursor in the synthesis of bioactive molecules, making it a valuable intermediate in organic synthesis.

Upstream product

• 155075-23-3 (2R,4R)-1-benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate 
• 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 

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.

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.

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