145451-97-4

Usage

Uses

Used in Pharmaceutical Industry:
(3R,4S,5R)-4-HYDROXY-5-[(1S)-1-HYDROXY-2-METHYLPROPYL]-3-METHYL-2-PYRROLIDINONE-5-CARBOXYLIC ACID is used as an intermediate in the synthesis of pharmaceutical compounds for various therapeutic applications. Its unique structure and functional groups allow for the development of new drugs with potential benefits in treating different medical conditions.
Used in Chemical Research:
In the field of chemical research, (3R,4S,5R)-4-HYDROXY-5-[(1S)-1-HYDROXY-2-METHYLPROPYL]-3-METHYL-2-PYRROLIDINONE-5-CARBOXYLIC ACID serves as a valuable compound for studying the properties and reactivity of complex organic molecules. Its unique stereochemistry and functional groups make it an interesting subject for research in organic chemistry, potentially leading to new discoveries and advancements in the field.
Used in Material Science:
(3R,4S,5R)-4-HYDROXY-5-[(1S)-1-HYDROXY-2-METHYLPROPYL]-3-METHYL-2-PYRROLIDINONE-5-CARBOXYLIC ACID can be used as a building block in the development of new materials with specific properties. Its unique structure and functional groups can be exploited to create materials with tailored characteristics, such as improved mechanical strength, thermal stability, or chemical resistance, for various applications in material science.
Used in Cosmetics Industry:
In the cosmetics industry, (3R,4S,5R)-4-HYDROXY-5-[(1S)-1-HYDROXY-2-METHYLPROPYL]-3-METHYL-2-PYRROLIDINONE-5-CARBOXYLIC ACID may be used as an ingredient in the formulation of cosmetic products. Its unique properties could potentially contribute to the development of innovative products with enhanced performance, such as improved skin hydration, anti-aging effects, or enhanced sensory experience.
Used in Environmental Applications:
(3R,4S,5R)-4-HYDROXY-5-[(1S)-1-HYDROXY-2-METHYLPROPYL]-3-METHYL-2-PYRROLIDINONE-5-CARBOXYLIC ACID could be utilized in the development of environmentally friendly products or processes. Its unique structure and functional groups may be harnessed to create biodegradable materials, contribute to waste reduction, or improve the efficiency of certain environmental processes.

InChI:InChI=1/C10H17NO5/c1-4(2)6(12)10(9(15)16)7(13)5(3)8(14)11-10/h4-7,12-13H,1-3H3,(H,11,14)(H,15,16)/t5-,6-,7+,10?/m1/s1

Upstream product

• 145451-95-2 (1S,6R,7S,7aS)-7a-(tert-Butyl-dimethyl-silanyloxymethyl)-7-hydroxy-1-isopropyl-6-methyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one 
• 876952-15-7 (2S,3S,4R)-2-((S)-1-benzoyloxy-2-methyl-propyl)-3-hydroxy-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid 
• 870527-57-4 (2R,3S)-(-)-2-azido-4-methyl-1-pentane-1,3-diol 
• 26291-75-8 (R)-1-((3aR,5S,6R,6aR)-2,2,6-trimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethane-1,2-diol 
• 145452-02-4 (1S,6R,7S,7aS)-7-Hydroxy-7a-hydroxymethyl-1-isopropyl-6-methyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one 
• 928209-79-4 2-(1-acetoxy-2-methyl-propyl)-3-hydroxy-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester 
• 928209-77-2 (2R,3S)-1-tert-butyl 2-methyl 2-((S)-1-acetoxy-2-methylpropyl)-3-hydroxy-5-oxopyrrolidine-1,2-dicarboxylate 
• 928209-78-3 2-(1-acetoxy-2-methyl-propyl)-3-hydroxy-4-methyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 1334590-08-7 (2R,3S)-1-tert-butyl 2-methyl 2-((S)-1-acetoxy-2-methylpropyl)-3-(tert-butyldimethylsilyloxy)-5-oxopyrrolidine-1,2-dicarboxylate 
• 1334589-99-9 (2R,3S)-methyl 3-(tert-butyldimethylsilyloxy)-2-((tert-butyl-dimethylsilyloxy)methyl)-5-oxopyrrolidine-2-carboxylate 
• 1334590-00-9 (2R,3S)-methyl 3-(tert-butyldimethylsilyloxy)-2-((tert-butyldimethylsilyloxy)methyl)-1-(4-methoxybenzyl)-5-oxopyrrolidine-2-carboxylate 
• 1334590-01-0 (2R,3S)-methyl 3-(tert-butyldimethylsilyloxy)-2-(hydroxy-methyl)-1-(4-methoxybenzyl)-5-oxopyrrolidine-2-carboxylate 

Downstream Products

• 133343-34-7 Lactacystin 
• 154226-60-5 omuralide 

Relevant academic research and scientific papers

Total Synthesis of Proteasome Inhibitor (-)-Omuralide through Asymmetric Ketene [2 + 2]-Cycloaddition

The total synthesis of (-)-omuralide, a potent specific proteasome inhibitor, has been achieved through an unprecedented route. The C3 and C4 chiral centers of the natural product have been selectively installed by an asymmetric [2 + 2]-cycloaddition betw

Application of Two Direct C(sp3)-H Functionalizations for Total Synthesis of (+)-Lactacystin

(Figure Presented). Herein, we report a new synthetic route from (S)-pyroglutaminol to (+)-lactacystin, a potent inhibitor of the 20S proteasome. The photoinduced intermolecular C(sp3)-H alkynylation and intramolecular C(sp3)-H acylation chemo- and stereoselectively constructed the tetra- and trisubstituted carbon centers, respectively. The obtained bicycle was transformed into the target compound in a concise manner. The present total synthesis demonstrates the power of the direct C(sp3)-H functionalizations for the assembly of multiple functionalized structures of natural products.

Stereospecific total syntheses of proteasome inhibitors omuralide and lactacystin

Omuralide, a transformation product of the microbial metabolite lactacystin, was the first molecule discovered as a specific inhibitor of the proteasome and is unique in that it specifically inhibits the proteolytic activity of the 20S subunit of the prot

Catalytic asymmetric total synthesis of (+)-lactacystin

Total synthesis of (+)-lactacystin, a potent and selective proteasome inhibitor, was accomplished using a catalytic enantioselective Strecker reaction of a ketoimine as the initial key step. An enone-derived N-phosphinoyl ketoimine 7 was selected as a sta

Enantioselective total syntheses of (-)-clasto-lactacystin β-lactone and 7-epi-(-)-clasto-lactacystin β-lactone

An alkylidene carbene 1,5-CH insertion has been used as a key step in an efficient enantioselective total synthesis of (-)-clasto-lactacystin β-lactone, and its C7-epimer. An additional noteworthy feature of the synthesis is the use of a novel oxidative deprotection procedure, utilizing DMDO, for the conversion of a late-stage benzylidene acetal into a primary alcohol and a secondary benzoate ester. The Royal Society of Chemistry 2006.

A concise route to (+)-lactacystin

A facile chromatography-free route to Kang's intermediate for the synthesis of (+)-lactacystin, a potent proteasome inhibitor, has been developed starting with Brown's asymmetric crotylation of tert-butyl 5-formyl-2,2-dimethyl-1,3- dioxan-5-ylcarbamate, e

A novel and efficient synthesis of a highly active analogue of clasto-lactacystin β-lactone

Herein, we describe a new convergent synthesis of a more potent analogue of clasto-lactacystin β-lactone (2), PS-519 compound 4, which is currently in preclinical development for the treatment of ischemia-reperfusion injury in stroke and myocardial infarction. The synthetic strategy relies on building two intermediates (an oxazoline and an aldehyde) which are joined through a doubly diastereoselective aldol reaction, setting up the requisite unichiral centers in the final product (4). The facial selectivity and ultimate stereocontrol are achieved by employing a trivalent aluminum Lewis acid, Me2AlCl, in a chelation-induced reaction which yields a single aldol adduct. The efficiency of the synthetic approach has allowed for the preparation of multigram quantities of clinical grade material, which will support Phase I studies.

Total synthesis of (+)-lactacystin

A double stereodifferentiating crotylation between aldehyde 1 and silane (S)-2 to afford homoallylic alcohol 3 is the key diastereoselective step (anti:syn > 30:1) in an efficient asymmetric synthesis of (+)-lactacystin. This compound is a metabolite isol

A new magnesium-catalyzed doubly diastereoselective anti-aldol reaction leads to a highly efficient process for the total synthesis of lactacystin in quantity

A new process is described for metal-catalyzed doubly diastereoselective Mukaiyama aldol coupling of a chiral tertiary α-amino aldehyde and an achiral silyl enol ether to form selectively an anti-aldol product. The metal requirement is strict, since of se

Stereoselective total synthesis of (+)-lactacystin from D-glucose

The chiral and stereoselective synthesis of (+)-lactacystin 1, the first non-protein neurotrophic factor having an α,α-disubstituted α- amino acid structure, is described. The highly functionalized γ- lactam portion possessing a tetra-substituted carbon w