109579-10-4

Basic information

• Product Name: tert-butyl (2S,3S)-2-benzyl-3-hydroxy-5-oxopyrrolidine-1-carboxylate(SALTDATA: FREE)
• Synonyms: tert-butyl (2S,3S)-2-benzyl-3-hydroxy-5-oxopyrrolidine-1-carboxylate(SALTDATA: FREE);tert-butyl rac-(2S,3S)-2-benzyl-3-hydroxy-5-oxopyrrolidine-1-carboxylate;(2S,3S)-TERT-BUTYL 2-BENZYL-3-HYDROXY-5-OXOPYRROLIDINE-1-CARBOXYLATE;tert-butyl (2S,3S)-2-benzyl-3-hydroxy-5-oxopyrrolidine-1-carboxylate(SALTDATA
• CAS NO: 109579-10-4
• Molecular Formula: C₁₆H₂₁NO₄
• Molecular Weight: 291.34224
• Mol File: 109579-10-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: tert-butyl (2S,3S)-2-benzyl-3-hydroxy-5-oxopyrrolidine-1-carboxylate(SALTDATA: FREE)(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl (2S,3S)-2-benzyl-3-hydroxy-5-oxopyrrolidine-1-carboxylate(SALTDATA: FREE)(109579-10-4)
• EPA Substance Registry System: tert-butyl (2S,3S)-2-benzyl-3-hydroxy-5-oxopyrrolidine-1-carboxylate(SALTDATA: FREE)(109579-10-4)

Safety Data

• Hazardous Substances Data: 109579-10-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Tert-butyl (2S,3S)-2-benzyl-3-hydroxy-5-oxopyrrolidine-1-carboxylate(SALTDATA: FREE) is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of novel drug candidates with potential therapeutic effects.
Used in Organic Chemistry:
In the field of organic chemistry, tert-butyl (2S,3S)-2-benzyl-3-hydroxy-5-oxopyrrolidine-1-carboxylate(SALTDATA: FREE) serves as a versatile building block for the creation of complex organic molecules, leveraging its unique functional groups to facilitate a range of chemical reactions and the formation of diverse molecular structures.
Used in Bioactive Molecule Synthesis:
Tert-butyl (2S,3S)-2-benzyl-3-hydroxy-5-oxopyrrolidine-1-carboxylate(SALTDATA: FREE) is employed as a precursor in the synthesis of bioactive molecules, capitalizing on its structural features to produce compounds with potential applications in medicine, agriculture, and other industries where bioactivity is crucial.

Upstream product

• 112700-41-1 (5S)-5-benzyl-1-(tert-butyloxycarbonyl)-4-hydroxy-1,5-dihydro-pyrrol-2-one 
• 24424-99-5 di-tert-butyl dicarbonate 
• 129029-32-9 (4S,5S)-5-Benzyl-2-oxo-4-hydroxypyrrolidine 
• 109579-09-1 (5S)-5-benzyl-4-hydroxy-1-t-butoxycarbonylpyrrol-2(5H)-one 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 55740-07-3 (4S)-4-benzyl-5-oxo-1,3-oxazolidine-3-carboxylic acid benzyl ester 
• 158257-34-2 (S)-5-benzyl-1-benzyloxycarbonyl-4-hydroxy-2,5-dihydropyrrol-2-one 
• 182567-73-3 (4S,5S)-1-benzyloxycarbonyl-5-benzyl-4-hydroxy-2-oxopyrrolidine 
• 220931-41-9 (S)-4-Benzyl-5-[1-ethoxycarbonyl-meth-(E)-ylidene]-oxazolidine-3-carboxylic acid benzyl ester 
• 175550-98-8 (2S,3R,4S)-2-Benzyl-3,4-dihydroxy-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 175550-94-4 (3S,4R,5S)-5-Benzyl-3,4-bis-benzyloxy-1-(4-methoxy-benzyl)-pyrrolidin-2-one 
• 175550-97-7 (3S,4R,5S)-5-Benzyl-3,4-bis-benzyloxy-pyrrolidin-2-one 
• 173728-51-3 (2S,3R,4S)-2-Benzyl-3,4-bis-benzyloxy-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 4530-18-1 N-(tert-butoxycarbonyl)-L-phenylalanine 

Downstream Products

• 101669-80-1 methyl (3S,4S)-N-tert-butoxycarbonyl-4-amino-3-hydroxy-5-phenylpentanoate 
• 148554-95-4 (3R,4S,5R)-N-(((tert)-butyloxy)carbonyl)-5-benzyl-4-hydroxy-3-(1-naphthylmethyl)-2-pyrrolidinone 
• 72155-48-7 (3S,4S)-4-tert-butoxycarbonylamino-3-hydroxy-5-phenylpentanoic acid 
• 129029-32-9 (4S,5S)-5-Benzyl-2-oxo-4-hydroxypyrrolidine 
• 175550-95-5 (2S,3S)-tert-butyl 2-benzyl-3-((tert-butyldimethylsilyl)oxy)-5-oxopyrrolidine-1-carboxylate 
• 247578-10-5 tert-butyl (2S,3S)-2-benzyl-3-hydroxypyrrolidine-1-carboxylate 
• 247578-12-7 (2S,3R)-3-Acetoxy-2-benzyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 247578-11-6 [(S)-1-((2S,3S)-2-Benzyl-3-hydroxy-pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid benzyl ester 
• 247578-13-8 Acetic acid (2S,3R)-2-benzyl-1-((S)-2-benzyloxycarbonylamino-3-methyl-butyryl)-pyrrolidin-3-yl ester 
• 125356-66-3 (+)-preussin 
• 158527-21-0 tert-butyl (2S,3S,5R)-2-benzyl-3-hydroxy-5-nonylpyrrolidine-1-carboxylate 
• 175550-96-6 (-)-(2S,3S,5R)-2-benzyl-3-(tert-butyldimethylsilyloxy)-5-nonylpyrrolidine-1-carboxylic acid tert-butyl ester 
• 148472-73-5 (2R,3S,4R)-4-(N-(((tert)-butyloxy)carbonyl)-amino)-2-amino-3-hydroxy-1-(1-naphthyl)-5-phenylpentane acetonide 
• 148472-67-7 (2R,3S,4R)-4-(N-(((tert)-butyloxy)carbonyl)-amino)-3-hydroxy-2-(1-naphthylmethyl)-5-phenylpentanoic acid acetonide 

Relevant articles and documents

An efficient approach to trans-4-hydroxy-5-substituted 2-pyrrolidinones through a stereoselective tandem Barbier process: divergent syntheses of (3R,4S)-statines, (+)-preussin and (?)-hapalosin

A diastereoselective approach to trans-4-hydroxy-5-substituted 2-pyrrolidinones 1 (P1 = TBS, P2 = H) has been developed through a stereoselective tandem Barbier process of (R,SRS)-8 with alkyl and aryl bromide. The stereochemistry at the C-5 stereogenic center of the trans-4-hydroxy-5-substituted 2-pyrrolidinones was solely controlled by α-alkoxy substitution. This effective approach was successfully used to prepare a variety of substituted (3R,4S)-statines 2. In addition, two bioactive natural products of (+)-preussin 4 and hapalosin 5 were effectively synthesized through this stereoselective tandem Barbier process.

A facile approach to trans-4,5-pyrrolidine lactam and application in the synthesis of nemonapride and streptopyrrolidine

An efficient approach to trans-4-hydroxylpyrrolidine lactams 1 starting from amino acid is described. The utility of this method has been demonstrated in the synthesis of antipsychotic nemonapride 3 and antiangiogenic streptopyrrolidine 4. Compared four s

PYRROLIDIN-3-YL COMPOUNDS USEFUL AS BETA-SECRETASE INHIBITORS FOR THE TREATMENT OF ALZHEIMER'S DISEASE

The present invention is directed to pyrrolidin-3-yl derivative compounds which are inhibitors of the beta-secretase enzyme and that are useful in the treatment of diseases in which the beta-secretase enzyme is involved, such as Alzheimer's disease. The i

Design of potential new HIV protease inhibitors: Enantioconvergent synthesis of new pyrrolidin-3-ol, and pyrrolidin-3-one peptide conjugates

Novel potential HIV protease inhibitors are obtained by an enantioconvergent synthesis of mimicking Phe-Pro dipeptides, achieved through the coupling between Boc(L)Phe or Boc(L)Tyr and both enantiomers of syn-2-benzylpyrrolidin-3-ol and their correspondin

A novel Wittig reaction of oxazolidinones: Stereospecific synthesis of N-BOC-(3S,4S)-statine and N-BOC-(3S,4S)-AHPPA

Stereospecific synthesis of N-BOC-(3S,4S)-Statine and N-BOC-(3S,4S)- AHPPA is achieved via a novel Wittig reaction of oxazolidinones in an efficient manner.

Hydroxyoxazolidines as alpha-aminoacetaldehye equivalents: novel inhibitors of calpain.

The synthesis of [1-[(5-hydroxy-4-(phenylmethyl)-3-oxazolidinyl)carbonyl]-2-ethylpropy lcarbamic acid phenylmethyl ester (2; MDL 104,903), a potent inhibitor of calpain, is described. Synthesis of related compounds, which offer insights into the mechanism of action for 2, are also described, as is an O-acetyl prodrug derivative of 2.

An improved procedure to homochiral cyclic statines

Chiral tetramic acids were prepared in high yields by the reaction of N-protected amino acids with Meldrum's acid employing DCC as a carboxyl activating agent. Reduction or hydrogenation of these tetramic acids produced homochiral cyclic statines.

A novel stereoselective synthesis of enantiomerically pure antifungal agent, (+)-preussin

An efficient and novel process is described for the asymmetric synthesis of (2S, 3S, 5R)-1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinol, (+)-preussin employing reductive deoxygenation of a functionalized quaternary α-hydroxy N-Boc pyrrolidine obtained by stereocontrolled elaboration of tri-O-benzyl-β-D-arabinofuranose. The synthetic strategy involves no separation of stereoisomers through the entire sequence.

Stereospecific Synthesis of N-Protected Statine and Its Analogues via Chiral Tetramic Acid

The condensation of a chiral N-protected amino acid with Meldrum's acid in the presence of isopropenyl chloroformate (IPCF) and of 4-N,N-dimethylaminopyridine (DMAP) has been examined.The cyclisation of the reaction product, by heating in an organic solve