1448706-36-2

Usage

Uses

Used in Pharmaceutical Research:
N-CBZ-trans-4-Hydroxy-D-prolinol is used as a chiral building block for the synthesis of various pharmaceuticals, agrochemicals, and other fine chemicals. Its stereochemical purity makes it a valuable starting material for the preparation of biologically active compounds.
Used in Organic Synthesis:
In the field of organic synthesis, N-CBZ-trans-4-Hydroxy-D-prolinol is utilized as a key intermediate in the preparation of complex organic molecules, contributing to the development of new drugs and other chemical products.
Used in Medicinal Chemistry:
N-CBZ-trans-4-Hydroxy-D-prolinol is used as a versatile chemical in medicinal chemistry due to its potential antiviral, antibacterial, and anti-inflammatory properties. Its investigation in these areas highlights its potential for the development of new therapeutic agents.
Used in Drug Development:
In the drug development industry, N-CBZ-trans-4-Hydroxy-D-prolinol is employed as a starting material for the synthesis of new drugs, particularly those targeting viral, bacterial, and inflammatory conditions. Its potential in these areas makes it a valuable asset in the discovery and development of novel therapeutic agents.

Upstream product

• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 64187-48-0 methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate 
• 501-53-1 benzyl chloroformate 
• 51-35-4 4R-4-hydroxyproline 
• 209269-34-1 N-CBZ-L-hydroxyproline 
• 197079-48-4 trans-N-(Benzyloxycarbonyl)-4-hydroxy-L-proline 
• 57653-35-7 (2S,4S)-4-hydroxypyrrolidine-1,2-dicarboxylic acid 1-benzyl 2-methyl 
• 1448706-35-1 C₂₁H₂₀N₂O₈ 
• 155075-23-3 (2R,4R)-1-benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate 
• 130930-25-5 (R,R)-4-hydroxy-1-(benzyloxycarbonyl)pyrrolidine-2-carboxylic acid 
• 3398-22-9 trans-4-hydroxyproline 
• 155153-78-9 (4S)-1-[(benzyloxy)carbonyl]-4-hydroxy-D-proline 
• 79433-95-7 (2R,4S)-1-benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate 
• 2584-71-6 cis-hydroxy-D-proline 

Downstream Products

• 192320-51-7 trans-4-hydroxy-(S)-Cbz-prolinal 
• 151953-64-9 (3R,5S)-5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}pyrrolidine-3-ol 
• 1448706-17-9 C₂₂H₂₃Cl₂N₃O₂S 
• 1448706-18-0 C₂₃H₂₅Cl₂N₃O₂S 
• 1009335-36-7 (3R,5R)-5-(hydroxymethyl)pyrrolidin-3-ol hydrochloride 
• 1448706-19-1 C₂₂H₂₃Cl₂N₃O₂S 
• 1448706-20-4 C₂₃H₂₅Cl₂N₃O₂S 
• 1018987-47-7 C₅H₁₁NO₂*ClH 
• 1253791-74-0 C₁₃H₁₈N₂O₃ 
• 13504-86-4 (2S,4S)-1-benzyloxycarbonyl-4-hydroxyproline 
• 1219963-29-7 (S)-benzyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(trifluoromethylsulfonyloxy)-2,5-dihydro-1H-pyrrole-1-carboxylate 

Relevant academic research and scientific papers

Practical Gram-Scale Synthesis of Iboxamycin, a Potent Antibiotic Candidate

A gram-scale synthesis of iboxamycin, an antibiotic candidate bearing a fused bicyclic amino acid residue, is presented. A pivotal transformation in the route involves an intramolecular hydrosilylation-oxidation sequence to set the ring-fusion stereocenters of the bicyclic scaffold. Other notable features of the synthesis include a high-yielding, highly diastereoselective alkylation of a pseudoephenamine amide, a convergent sp3-sp2 Negishi coupling, and a one-pot transacetalization-reduction reaction to form the target compound's oxepane ring. Implementation of this synthetic strategy has provided ample quantities of iboxamycin to allow for its in vivo profiling in murine models of infection.

LINCOSAMIDE ANTIBIOTICS AND USES THEREOF

Provided are compounds of Formula (I) for the treatment of infectious and inflammatory diseases. The compounds described herein are lincosamides modified at the amino acid (southern) region. The compounds may have further modification at the C-7 position of the aminooctose (northern) region, thus distinguishing them from lincomycin and clindamycin. Also provided are methods for preparing the compounds, pharmaceutical compositions comprising the compounds, and methods of treating infectious diseases using the disclosed compounds.

FUSED HETEROCYCLIC BENZODIAZEPINE DERIVATIVES AND USES THEREOF

The present disclosure provides compounds and compositions capable of extending lifespan, and methods of use thereof.

NOVEL BENZODIAZEPINE DERIVATIVES AND USES THEREOF

The present disclosure provides compounds and compositions capable of extending lifespan, and methods of use thereof.

Scale-up Synthesis of Tesirine

This work describes the enabling synthesis of tesirine, a pyrrolobenzodiazepine antibody-drug conjugate drug-linker. Over the course of four synthetic campaigns, the discovery route was developed and scaled up to provide a robust manufacturing process. Early intermediates were produced on a kilogram scale and at high purity, without chromatography. Midstage reactions were optimized to minimize impurity formation. Late stage material was produced and purified using a small number of key high-pressure chromatography steps, ultimately resulting in a 169 g batch after 34 steps. At the time of writing, tesirine is the drug-linker component of eight antibody-drug conjugates in multiple clinical trials, four of them pivotal.

An Immucillin-Based Transition-State-Analogous Inhibitor of tRNA-Guanine Transglycosylase (TGT)

Shigellosis is one of the most severe diarrheal diseases worldwide without any efficient treatment so far. The enzyme tRNA-guanine transglycosylase (TGT) has been identified as a promising target for small-molecule drug design. Herein, we report a transition-state analogue, a small, immucillin-derived inhibitor, as a new lead structure with a novel mode of action. The complex inhibitor synthesis was accomplished in 18 steps with an overall yield of 3 %. A co-crystal structure of the inhibitor bound to Z. mobilis TGT confirmed the predicted conformation of the immucillin derivative in the enzyme active site.

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.

New optically active 4-alkoxyprolinol ethers derived from trans-4-Hydroxy-L-proline

(2S,4R)-trans-4-Hydroxy-L-proline has been used as thechiral-pool source in the efficient syntheses of optically active protected 4-hydroxyprolinols. After N-acyl protection andester formation, the first ether moiety was introduced maintaining the chiral

Synthesis of (2S,4S)-4-hydroxyproline from D-glucose

Diacetone-D-glucose 1 gives 3-O-methylxanthate 2 on reaction with NaH=Me I. Reductive deoxygenation of compound 2 by Bu3SnH gives the corresponding 3-deoxy glucose derivative 3 and on acid-catalyzed regioselective deprotection of C-5,6-acetonide gives the diol 4. The diol on oxidative cleavage with NaIO4 gives the aldehyde 5, which on further condensation with benzylamine followed by reduction with NaBH4 gives the amine 7. Z-Protection of the amine followed by methanolysis gives methyl furanoside 9. Reaction of 9 with methanesulfonyl chloride=Et3N gives the corresponding C-3-O-mesylate derivative 10. Catalytic hydrogenation of compound 10 (Pd=C=H2=MeOH 3 kg) gives bicyclic oxaazo compound 11, due to deprotection of the N-benzyl- and Z-protecting groups and intramolecular nucleophilic displacement of the C-2-O-mesylate by the C-5 amine in a one-pot reaction. Z-Protection of the amine 11 followed by acid-catalyzed hydrolysis gives acetal 13. Reduction of acetal by use of NaBH4 gives Z-prolinol 14. Selective oxidation of diol 14 by (2,2,6,6-tetramethylpiperidin-1-yl)-oxyl (TEMPO)=[(bis)(acetoxy)iodo]-benzene (BAIB) and NaClO2=NaH 2PO4, followed by Z-deprotection, gives the title compound I in 3.5% overall yield from D-glucose. Copyright Taylor & Francis Group, LLC.

AURORA KINASE COMPOUNDS AND METHODS OF THEIR USE

Provided herein are pyrrolotriazine compounds for treatment of Aurora kinase mediated diseases. Also provided are pharmaceutical compositions comprising the compounds and methods of using the compounds and compositions.