56881-90-4

Basic information

• Product Name: (R)-(+)-ALPHA-HYDROXY-GAMMA-BUTYROLACTONE
• Synonyms: RARECHEM AK HZ 0027;(R)-(+)-DIHYDRO-3-HYDROXY-2(3H)-FURANONE;(R)-2-HYDROXYBUTYROLACTONE;(R)-2-HYDROXY-GAMMA-BUTYROLACTONE;(R)-(+)-3-HYDROXYTETRAHYDROFURAN-2-ONE;(R)-(+)-ALPHA-HYDROXY-GAMMA-BUTYROLACTONE;2(3H)-FURANONE, DIHYDRO-3-HYDROXY-, (R);(R)-(+)-α-Hydroxy-γ-butyrolactone
• CAS NO: 56881-90-4
• Molecular Formula: C₄H₆O₃
• Molecular Weight: 102.09
• Product Categories: Small molecule;Chiral Building Blocks;Simple Alcohols (Chiral);Synthetic Organic Chemistry
• Mol File: 56881-90-4.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 133 °C10 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.309 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.467(lit.)
• Storage Temp.: 2-8°C
• PKA: 13.07±0.20(Predicted)
• BRN: 80588
• CAS DataBase Reference: (R)-(+)-ALPHA-HYDROXY-GAMMA-BUTYROLACTONE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-ALPHA-HYDROXY-GAMMA-BUTYROLACTONE(56881-90-4)
• EPA Substance Registry System: (R)-(+)-ALPHA-HYDROXY-GAMMA-BUTYROLACTONE(56881-90-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 56881-90-4(Hazardous Substances Data)

Usage

Uses

(R)-(+)-α-Hydroxy-γ-butyrolactone can be used as a starting material to synthesize: δ-Azaproline by reacting with benzyloxycarbonyl aminophthalimide via Mitsunobu reactions. Homochiral (R)-2,4-dihydroxybutyramide seco-pseudonucleoside reagents. Botryolide B via esterification and ring-closing metathesis reaction.Pregnane derivatives containing γ-butyrolactones as potential glucocorticoid agonists.

Upstream product

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

Downstream Products

• 905725-83-9 (2R)-N-[2-(imidazol-4-yl)ethyl]-2,4-dihydroxybutyramide 
• 883998-38-7 (R)-α-methoxy-γ-butyrolactone 
• 1190788-43-2 (S)-α-(N-benzyloxycarbonylaminophthalimido)-γ-butyrolactone 
• 1190832-67-7 (R)-α-benzyloxy-γ-butyrolactone 
• 168982-69-2 N-(3-oxododecanoyl)-L-homoserine lactone 
• 669000-31-1 (R)-3-(tert-butyldimethylsilyloxy)dihydrofuran-2(3H)-one 
• 1398752-10-7 methyl (2R)-2-hydroxy-4-iodobutanoate 
• 1433891-89-4 (S)-3-(4-bromo-2-fluorophenoxy)dihydrofuran-2(3H)-one 
• 1003888-29-6 (R)-4-nitrophenyl (2-oxotetrahydrofuran-3-yl)carbonate 
• 1351168-60-9 (S)-3-(4-bromo-2-fluoro-5-methylphenoxy)dihydrofuran-2(3H)-one 
• 1351168-35-8 (S)-3-(6-bromopyridin-3-yloxy)dihydrofuran-2(3H)-one 
• 943654-12-4 (S)-3-(4-chloro-5-fluoroindolin-1-yl)-dihydrofuran-2(3H)-one 
• 220352-11-4 (R)-dihydro-3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2(3H)-furanone 
• 883998-35-4 (R)-2-hydroxy-4-(naphthalen-2-ylthio)butanoic acid 

Relevant articles and documents

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.

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.

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.