105526-85-0

Basic information

• Product Name: (S)-(+)-5-(TRITYLOXYMETHYL)-2-PYRROLIDONE
• Synonyms: L-5-TRITYLOXYMETHYL-2-PYRROLIDINONE;O-TRITYL-L-PYROGLUTAMINOL;(S)-(+)-5-(TRITYLOXYMETHYL)-2-PYRROLIDINONE;(S)-(+)-5-(TRITYLOXYMETHYL)-2-PYRROLIDONE;Zinc04202546;(S)-5-(triphenylMethoxyMethyl)pyrrolidin-2-one;O-Trityl-L-Pyroglutaminol≥ 99% (HPLC);(S)-5-((trityloxy)methyl)pyrrolidin-2-one(WX191578)
• CAS NO: 105526-85-0
• Molecular Formula: C₂₄H₂₃NO₂
• Molecular Weight: 357.44
• Product Categories: Chiral Building Blocks;Heterocyclic Building Blocks;Pyrrolidines
• Mol File: 105526-85-0.mol

Chemical Properties

• Melting Point: 164-166 °C(lit.)
• Boiling Point: 533°Cat760mmHg
• Flash Point: 276.1°C
• Appearance: /
• Density: 1.142g/cm³
• Vapor Pressure: 1.94E-11mmHg at 25°C
• Refractive Index: 1.591
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 15.80±0.40(Predicted)
• CAS DataBase Reference: (S)-(+)-5-(TRITYLOXYMETHYL)-2-PYRROLIDONE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-5-(TRITYLOXYMETHYL)-2-PYRROLIDONE(105526-85-0)
• EPA Substance Registry System: (S)-(+)-5-(TRITYLOXYMETHYL)-2-PYRROLIDONE(105526-85-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 105526-85-0(Hazardous Substances Data)

Usage

Uses

Used in Asymmetric Diels-Alder Reactions:
(S)-(+)-5-(TRITYLOXYMETHYL)-2-PYRROLIDONE is used as a chiral auxiliary for asymmetric Diels-Alder reactions. Its application reason is to facilitate the selective formation of desired diastereomers with high enantioselectivity and diastereoselectivity, which is crucial in the synthesis of complex organic molecules and pharmaceuticals.
Used in Asymmetric Conjugate Additions:
In the field of asymmetric conjugate additions, (S)-(+)-5-(TRITYLOXYMETHYL)-2-PYRROLIDONE is utilized as a chiral auxiliary. The application reason is to enhance the stereoselectivity of the reaction, allowing for the preferential formation of one enantiomer over the other, which is essential in the production of enantiomerically pure compounds for various applications, including pharmaceuticals and agrochemicals.
Used in Pharmaceutical Industry:
(S)-(+)-5-(TRITYLOXYMETHYL)-2-PYRROLIDONE is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its application reason is to provide a chiral center that can be further modified or functionalized to create biologically active molecules with potential therapeutic properties.
Used in Chemical Research and Development:
In the research and development sector, (S)-(+)-5-(TRITYLOXYMETHYL)-2-PYRROLIDONE is employed as a valuable building block for the creation of novel chiral molecules. Its application reason is to explore new chemical reactions and develop innovative synthetic routes for the production of enantiomerically pure compounds with potential applications in various industries, such as pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C24H23NO2/c26-23-17-16-22(25-23)18-27-24(19-10-4-1-5-11-19,20-12-6-2-7-13-20)21-14-8-3-9-15-21/h1-15,22H,16-18H2,(H,25,26)/t22-/m0/s1

Upstream product

• 865-34-9 lithium methanolate 
• 128791-81-1 (1R,2R,3R,4S)-3-((S)-2-Oxo-5-trityloxymethyl-pyrrolidine-1-carbonyl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester 
• 15082-42-5 lithium benzyloxide 
• 128791-80-0 (S)-1-((1S,2R,3R,4R)-3-Phenyl-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-5-trityloxymethyl-pyrrolidin-2-one 
• 52203-12-0 Lithium allyl alcoholate 
• 117005-89-7 (5S)-1-[(3S)-3-(dimethyl(phenyl)silyl)butanoyl]-5-(triphenylmethoxymethyl)pyrrolidin-2-one 
• 76-83-5 trityl chloride 
• 17342-08-4 (S)-Pyroglutaminol 
• 107-18-6 allyl alcohol 
• 100-51-6 benzyl alcohol 
• 98-79-3 L-Pyroglutamic acid 
• 128791-78-6 (E)-4-Oxo-4-((S)-2-oxo-5-trityloxymethyl-pyrrolidin-1-yl)-but-2-enoic acid methyl ester 
• 128822-03-7 (5S)-N-[(2E)-3-phenylprop-2-enoyl]-5-triphenylmethoxymethyl-2-pyrrolidinone 
• 56-86-0 L-glutamic acid 

Downstream Products

• 164070-83-1 (5S)-1-<(2E)-3-Trimethylsilylprop-2-enoyl>-5-(triphenylmethoxymethyl)pyrrolidin-2-one 
• 164203-10-5 (S)-1-[(E)-3-(Dimethyl-phenyl-silanyl)-acryloyl]-5-trityloxymethyl-pyrrolidin-2-one 
• 130696-99-0 (S)-1-[(Z)-3-(Dimethyl-phenyl-silanyl)-acryloyl]-5-trityloxymethyl-pyrrolidin-2-one 
• 215389-45-0 (2'E,5S)-1-(Hepta-2',6'-dienoyl)-5-triphenylmethoxymethylpyrrolidin-2-one 
• 117005-89-7 (5S)-1-[(3S)-3-(dimethyl(phenyl)silyl)butanoyl]-5-(triphenylmethoxymethyl)pyrrolidin-2-one 
• 105526-91-8 (S)-1-((R)-3-Methyl-pentanoyl)-5-trityloxymethyl-pyrrolidin-2-one 
• 105526-94-1 (S)-1-((S)-3-Cyclohexyl-heptanoyl)-5-trityloxymethyl-pyrrolidin-2-one 
• 105526-92-9 (S)-1-((S)-3-Methyl-pent-4-enoyl)-5-trityloxymethyl-pyrrolidin-2-one 
• 105526-92-9 (S)-1-((R)-3-Methyl-pent-4-enoyl)-5-trityloxymethyl-pyrrolidin-2-one 
• 105526-95-2 (S)-1-((R)-3-Ethyl-heptanoyl)-5-trityloxymethyl-pyrrolidin-2-one 
• 105526-95-2 (S)-1-((S)-3-Ethyl-heptanoyl)-5-trityloxymethyl-pyrrolidin-2-one 
• 105526-89-4 (S)-1-((S)-3-Cyclohexyl-butyryl)-5-trityloxymethyl-pyrrolidin-2-one 
• 105526-89-4 (S)-1-((R)-3-Cyclohexyl-butyryl)-5-trityloxymethyl-pyrrolidin-2-one 
• 105526-96-3 (S)-5-Trityloxymethyl-1-((R)-3-vinyl-heptanoyl)-pyrrolidin-2-one 

Relevant articles and documents

Novel Compounds 002

Compounds of Formulae I, or pharmaceutically acceptable salts thereof: wherein R1, R2 and Y are as defined in the specification as well as salts and pharmaceutical compositions including the compounds are prepared. They are useful in therapy, in particular in the management of pain.

High ?-Facial Selectivity Through Chelation of Magnesium Ions in the DMD Epoxidation of α,β-Unsaturated Imides with Chiral Pyrrolidinone Auxiliaries

High diastereoselectivity, nut of the opposite sense, is observed in the epoxidation (DMD or mCPBA) of α,β-unsaturated imides equipped with pyrrolidinone-type chiral auxiliaries that bear either a hydroxymethyl or trityloxymethyl side chain. This unprecedented reversed ?-facial differentiation is promoted by chelation of a magnesium ion, which results in conformational control over the essential steric interactions.

Electrophilic fluorination of pyroglutamic acid derivatives: Application of substrate-dependent reactivity and diastereoselectivity to the synthesis of optically active 4-fluoroglutamic acids

Electrophilic fluorination of enantiomerically pure 2-pyrrolidinones (4) derived from (L)-glutamic acid has been investigated as a method for the synthesis of single stereoisomers of 4-fluorinated glutamic acids. Reaction of the lactam enolate derived from 9 with NFSi results in a completely diastereoselective monofluorination reaction to yield the monocyclic trans-substituted α-fluoro lactam product 21. Unfortunately, a decreased kinetic acidity in 21 and other structurally related monofluorinated products renders them resistant to a second fluorination. In contrast, the bicyclic lactam 12 is readily difluorinated under the standard conditions described to yield the α,α-difluoro lactam 24. The difference in reactivity between the two types of related lactams is attributed mainly to the presence or lack of a steric interaction between the base used for deprotonation and the protecting group present in the pyrrolidinone substrates. This conclusion was reached based on analysis of the X-ray crystal structure of 21, molecular modeling, and experimental evidence. The key intermediates 21 and 24 are converted to (2S,4R)-4-fluoroglutamic acid and (2S)-4,4-difluoroglutamic acid, respectively.

Syntheses of 2-[(1S,3S)-1-amino-3-carboxy-3-hydroxypropyl]-thiazole-4-carboxylic acid and the tripeptide skeleton of nosiheptide containing the acid

The stereoselective synthesis of an amino acid component called Fragment D, N,O-diprotected 2-[(1S,3S)-1-amino-3-carboxy-3-hydroxypropyl]thiazole-4-carboxylic acid of a macrobicyclic peptide antibiotic nosiheptide, was achieved by two routes. The dipeptide, Fragment B-C, 2-[(Z)-1-(N,O-isopropylidene-L-threonylamino)-1-propenyl]thiazole-4-ca rboxylic acid was also synthesized by the thiazole ring formation from (Z)-2-(N,O-diprotected L-threonylamino)-2-butenethioamide with ethyl bromopyruvate. The coupling of two components by using a condensing agent gave the expected tripeptide 2, which is an important partial skeleton of the nosiheptide.

Diastereoselectivity in the Preparation of β-Silyl Esters from αβ-Unsaturated Esters and Amides Attachhed to Chiral Auxiliaries

The conjugate addition of the phenyldimethylsilyl-cuprate reagent to cinnamate and crotonate esters and amides 1 of various known chiral auxiliaries, a-e, is diastereoselective.The sense of diastereoselectivity of silyl-cuprate addition to the esters 1b-d, 8 and 9 is different from established precedent based on carbon-cuprates, but is normal for silyl-cuprate addition to the amide 1a, the imines 1e and 21, and the oxazolidine 6.The chiral auxiliary e gives the best results of those tested, and the silicon-containing group can be removed from the chiral auxiliary using alkoxide ion in aprotic media, making available β-silyl esters 27-29 of high enantiomeric excess, with recovery of the chiral auxiliary 30.

Asymmetric Diels-Alder Reaction with use of (S)-5-(Trityloxymethyl)pyrrolidin-2-one as a Chiral Auxiliary

(S)-5-(Trityloxymethyl)pyrrolidin-2-one (1) is an efficient and recyclable chiral auxiliary in the asymmetric Diels-Alder reaction of the imide (2) with dienes, affording cycloadducts (3) with excellent diastereofacial selectivity.

Diastereoselectivity in the Preparation of β-Silylesters from αβ-Unsaturated Esters and Amides Attached to Chiral Auxiliaries

The conjugate addition of the phenyldimethylsilyl-cuprate reagent to cinnamate and crotonate esters and amides of various known chiral auxiliaries is diastereoselective, making available β-silylesters of high enantiomeric excess; the sense of the diastereoselectivity is anomalously different from established precedent in the case of silyl-cuprate addition to the cinnamate ester (1, R = Ph, R* = d).

ASYMMETRIC CONJUGATE ADDITION REACTION BY THE USE OF (S)-γ-TRITYLOXYMETHYL-γ-BUTYROLACTAM AS A CHIRAL AUXILIARY

(S)-γ-Trityloxymethyl-γ-butyrolactam (2) serves as a chiral auxiliary in the conjugate addition reaction of the corresponding imide (3) of α,β-unsaturated carboxylic acids with Grignard reagents in the presence of CuBr-SMe2 in THF to give, after hydrolysis, the β,β-disubstituted carboxylic acids (5) with predictable absolute configuration and high enantiomeric excess.