52079-23-9

Usage

Uses

1. Organic Synthesis:
(S)-(-)-alpha-Hydroxy-gamma-butyrolactone is used as an intermediate in organic synthesis for the production of various compounds.
2. Pharmaceutical Industry:
Used in Pharmaceutical Industry:
(S)-(-)-alpha-Hydroxy-gamma-butyrolactone is used as a key component in the synthesis of the polyether antibiotic monensin, which is effective against certain bacterial infections.
3. Vitamin D Analogs:
Used in Pharmaceutical Industry:
(S)-(-)-alpha-Hydroxy-gamma-butyrolactone is used as a building block for the functionalized D-ring side chains of vitamin D analogs, which have potential applications in treating various health conditions related to vitamin D deficiency.
4. Pesticides:
Used in Agriculture Industry:
(S)-(-)-alpha-Hydroxy-gamma-butyrolactone is used as a starting material in the development of new pesticides, contributing to the creation of more effective and environmentally friendly solutions for pest control.

InChI:InChI=1/C4H6O3/c5-3-1-2-7-4(3)6/h3,5H,1-2H2/t3-/m0/s1

Upstream product

• 76224-59-4 (R)-2-Acetoxy-4-hydroxy-butyric acid ethyl ester 
• 135247-43-7 methyl 2,4-dihydroxybutanoate 
• 124724-88-5 (5S)-5-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-one 
• 153011-57-5 (5S)-(2,2-Cyclohexylidene-4-oxo-1,3-dioxolan-5-yl)acetic acid 
• 617-55-0 dimethyl (S)-malate 
• 97-67-6 (S)-Malic acid 
• 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 
• 4744-10-9 dimethoxypropane 
• 104-15-4 toluene-4-sulfonic acid 
• 617-48-1 malic acid 
• 153011-58-6 (5S)-(1'-Hydroxyethyl)-2,2-cyclohexylidene-1,3-dioxolan-4-one 

Downstream Products

• 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 
• 1190788-43-2 (S)-α-(N-benzyloxycarbonylaminophthalimido)-γ-butyrolactone 
• 1190832-67-7 (R)-α-benzyloxy-γ-butyrolactone 
• 86677-74-9 2(R)-fluoro-γ-butyrolactone 
• 163181-96-2 (S)-3-(benzyloxy)dihydrofuran-2(3H)-one 
• 666706-29-2 (R)-α-N,N-diboc-aminoxy-γ-butyrolactone 
• 1131164-81-2 (3S)-3-triethylsilanyldihydrofuran-2(3H)-one 
• 153944-88-8 (S)-(-)-2,4-Dihydroxy-N,N-dimethylbutyramid 
• 130626-32-3 (S)-(-)-3-<(2-Methoxyethoxy)methoxy>-2-oxolanone 
• 73991-96-5 (S)-3-hydroxybutyrolactone, benzyloxy methyl ether 
• 56881-91-5 3-(Tetrahydro-pyran-2-yloxy)-dihydro-furan-2-one 
• 56881-91-5 (S)-3-(Tetrahydro-pyran-2-yloxy)-dihydro-furan-2-one 

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.

SYNTHETIC PRECURSOR OF EPOTHILONE FOR IMPROVING PRODUCTION OF EPOTHILONE AND METHOD FOR PREPARING EPOTHILONE USING THE SAME

The present invention relates to a compound for increasing production of epothilone in actinomyces, and to a method for producing epothilone with increased yield. The method for producing epothilone of the present invention includes a step of culturing actinomyces in which epothilone-biosynthesizing genes in Sorangium cellulosum including epoD, epoE, epoF, orf6, orf3, and orf14 are introduced in a culture medium. According to the present invention, it is possible to increase the production yield of epothilone in actinomyces, even in actinomyces in which epoA, epoP, epoB, and epoC are not introduced therein.COPYRIGHT KIPO 2016

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.

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.

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.

Studies towards the total synthesis of (-)-caulerpenynol, a toxic sesquiterpenoid of the green seaweed caulerpa taxifolia

The first diastereoselective synthesis of the antimicrobial and cytotoxic agent (-)-caulerpenynol (2) was achieved in relatively few steps from, commercially available (S)-malic acid, Highlights of this synthesis include the nonracemization. of the sensitive a-hydroxy ketone moiety and the proper choice of the protecting groups for critical last deprotection step. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009.

Enantioselective synthesis of the PPARα agonist (R)-K-13675 via (S)-2-hydroxybutyrolactone

Enantioselective synthesis of enantiomerically pure PPARα agonist (R)-K-13675 can be achieved starting from (S)-2-hydroxybutyrolactone. An important intermediate, 2-(aryloxy)butyrolactone, was prepared by reaction of the phenol with (S)-2-hydroxybutyrolactone in excellent yield without loss of enantiomeric purity using the Mitsunobu reaction, followed by conversion into the 2-(aryloxy)butanoic acid via the 2-(aryloxy)-4-iodobutanoate by cleavage of the lactone on exposure to iodotrimethylsilane, followed by hydrogenolysis and hydrolysis. Georg Thieme Verlag Stuttgart.