56881-90-4

Usage

Uses

Used in Pharmaceutical Industry:
(R)-(+)-ALPHA-HYDROXY-GAMMA-BUTYROLACTONE is used as a starting material for the synthesis of various pharmaceutical compounds, including:
1. δ-Azaproline: It is synthesized by reacting (R)-(+)-ALPHA-HYDROXY-GAMMA-BUTYROLACTONE with benzyloxycarbonyl aminophthalimide via Mitsunobu reactions. δ-Azaproline is a valuable building block for the development of novel pharmaceutical agents.
2. Homochiral (R)-2,4-dihydroxybutyramide seco-pseudonucleoside reagents: These reagents are synthesized from (R)-(+)-ALPHA-HYDROXY-GAMMA-BUTYROLACTONE and are used in the development of new nucleoside analogs with potential therapeutic applications.
3. Botryolide B: (R)-(+)-ALPHA-HYDROXY-GAMMA-BUTYROLACTONE is synthesized through esterification and ring-closing metathesis reactions starting from (R)-(+)-ALPHA-HYDROXY-GAMMA-BUTYROLACTONE. Botryolide B has potential applications in the pharmaceutical industry as a bioactive molecule.
4. Pregnane derivatives containing γ-butyrolactones: These derivatives are synthesized from (R)-(+)-ALPHA-HYDROXY-GAMMA-BUTYROLACTONE and are being investigated as potential glucocorticoid agonists, which could have applications in the treatment of various inflammatory and immune disorders.

Upstream product

• 76224-59-4 (R)-2-Acetoxy-4-hydroxy-butyric acid ethyl ester 
• 25409-36-3 3-hydroxy-2,5-dihydrofuran-2-one 
• 617-48-1 malic acid 
• 174563-88-3 (5R)-5-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-one 
• 117-34-0 2,2-diphenylacetic acid 
• 19444-84-9 3-hydroxyoxolan-2-one 
• 1538-75-6 2,2-dimethylpropanoic anhydride 
• 76-86-8 Triphenylsilyl chloride 
• 73991-95-4 2-[(4R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]acetic acid 
• 135247-43-7 methyl 2,4-dihydroxybutanoate 
• 71385-84-7 α-acetonyl-γ-butyrolactone 
• 112709-23-6 2-O-acetyl-3-deoxy-D-glycero-tetronolactone 

Downstream Products

• 120964-19-4 (R)-4-Oxo-2-(tetrahydro-pyran-2-yloxy)-butyric acid benzyl ester 
• 86677-82-9 2,3-dideoxy-2-fluoro-L-glycero-tetronolactone 
• 192057-37-7 methanesulfonic acid (3R)-2-oxotetrahydrofuran-3-yl ester 
• 586976-83-2 (R)-3-Methoxymethoxy-dihydro-furan-2-one 
• 112709-23-6 2-O-acetyl-3-deoxy-D-glycero-tetronolactone 
• 905725-83-9 (2R)-N-[2-(imidazol-4-yl)ethyl]-2,4-dihydroxybutyramide 
• 905725-67-9 (2R)-N-methyl-N-(2-methylaminoethyl)-2,4-dihydroxybutyramide 
• 666706-28-1 (R)-toluene-4-sulfonic acid 2-oxo-tetrahydrofuran-3-yl ester 
• 883998-38-7 (R)-α-methoxy-γ-butyrolactone 
• 943654-10-2 (S)-3-(6-chloro-3,4-dihydroquinolin-1(2H)-yl)-dihydrofuran-2(3H)-one 
• 1190832-67-7 (R)-α-benzyloxy-γ-butyrolactone 
• 669000-31-1 (R)-3-(tert-butyldimethylsilyloxy)dihydrofuran-2(3H)-one 
• 168982-69-2 N-(3-oxododecanoyl)-L-homoserine lactone 

Relevant academic research and scientific papers

Preparation method of alpha-hydroxyl-gamma-butyrolactone

The invention belongs to the field of preparation of organic compounds, and provides a preparation method of alpha-hydroxyl-gamma-butyrolactone. The method is characterized in that malic acid is used as a raw material, and alpha-hydroxyl-gamma-butyrolactone is synthesized with high yield through four steps of reactions, namely, carboxyl and alpha-hydroxyl protection, beta-carboxyl reduction, protecting group removal and internal esterification. The method has the advantages of easily available raw materials, mild reaction conditions and low cost, and is suitable for large-scale preparation of alpha-hydroxy-gamma-butyrolactone.

CYCLIC PHOSPHATE SUBSTITUTED NUCLEOSIDE DERIVATIVES AND METHODS OF USE THEREOF FOR THE TREATMENT OF VIRAL DISEASES

The present invention relates to Cyclic Phosphate Substituted Nucleoside Derivatives of Formula (I), and pharmaceutically acceptable salts thereof, wherein A, B, Q, V, R1, R2 and R3 are as defined herein. The present invention also relates to compositions comprising a Cyclic Phosphate Substituted Nucleoside Derivative, and methods of using the Cyclic Phosphate Substituted Nucleoside Derivatives for treating or preventing HCV infection in a patient.

Silylation-based kinetic resolution of α-hydroxy lactones and lactams

A silylation-based kinetic resolution has been developed for α-hydroxy lactones and lactams employing the chiral isothiourea catalyst (-)-benzotetramisole and triphenylsilyl chloride as the silyl source. The system is more selective for lactones than lactams, and selectivity factors up to 100 can be achieved utilizing commercially available reagents.

Kinetic resolution of racemic 2-hydroxy-γ-butyrolactones by asymmetric esterification using diphenylacetic acid with pivalic anhydride and a chiral acyl-transfer catalyst

Various optically active 2-hydroxy-γ-butyrolactone derivatives are produced via the kinetic resolution of racemic 2-hydroxy-γ-butyrolactones with diphenylacetic acid using pivalic anhydride and (R)-benzotetramisole ((R)-BTM), a chiral acyl-transfer catalyst. Importantly, the substrate scope of this novel protocol is fairly broad (12 examples, s-value; up to over 1000). In addition, we succeeded in disclosing the reaction mechanism to afford high enantioselectivity using theoretical calculations and expounded on the substituent effects at the C-3 positions in 2-hydroxylactones.

Modular and stereoselective synthesis of tetrasubstituted helical alkenes via a palladium-catalyzed domino reaction

A highly modular and stereoselective synthesis of tetrasubstituted helical alkenes is accomplished by a Pd-catalyzed norbornene-mediated domino reaction. This protocol features the rapid assembly of four C-C bonds via sequential C-H activations and carbopalladations along with efficient access to enantiopure bromoalkyl aryl alkyne precursors using homologative alkynylation as the key transformation. Three distinct elements of stereoselectivity were observed in the preparation of the chiral helical alkenes: retention of stereochemistry of the substrates, induced helical diastereoselectivity in the alkene formation, and the exclusive exo-facial selectivity of the norbornene incorporation.

HETEROCYCLIC DERIVATIVES AS MODULATORS OF ION CHANNELS

The present invention relates to heterocyclic derivatives useful as inhibitors of ion channels. The invention also provides pharmaceutically acceptable compositions comprising the compounds of the invention and methods of using the compositions in the treatment of various disorders.

HETEROCYCLIC DERIVATIVES AS MODULATORS OF ION CHANNELS

The present invention relates to heterocyclic derivatives useful as inhibitors of ion channels. The invention also provides pharmaceutically acceptable compositions comprising the compounds of the invention and methods of using the compositions in the treatment of various disorders.

A surprising mechanistic "switch" in Lewis acid activation: A bifunctional, asymmetric approach to α-hydroxy acid derivatives

We report a detailed synthetic and mechanistic study of an unusual bifunctional, sequential hetero-Diels-Alder/ring-opening reaction in which chiral, metal complexed ketene enolates react with o-quinones to afford highly enantioenriched, α-hydroxylated carbonyl derivatives in excellent yield. A number of Lewis acids were screened in tandem with cinchona alkaloid derivatives; surprisingly, trans-(Ph3P)2PdCl2 was found to afford the most dramatic increase in yield and rate of reaction. A series of Lewis acid binding motifs were explored through molecular modeling, as well as IR, UV, and NMR spectroscopy. Our observations document a fundamental mechanistic "switch", namely the formation of a tandem Lewis base/Lewis acid activated metal enolate in preference to a metal-coordinated quinone species (as observed in other reactions of o-quinone derivatives). This new method was applied to the syntheses of several pharmaceutical targets, each of which was obtained in high yield and enantioselectivity.

Epothilon derivatives, method for the production and the use thereof as pharmaceuticals

Disclosed are epothilone compounds of formula I, which are useful as pharmaceutical compounds for treating, for example, malignant tumors and chronic inflammatory diseases and are useful in anti-angiogenesis therapy.

A METHOD OF PREPARING ENANTIOMERS OF INDOLE-2,3-DIONE-3-OXIME DERIVATIVES

The present invention is directed to a method of preparing enantiomers of indole-2,3-dione-3-oxime derivatives.