30608-62-9

Usage

Uses

Used in Pharmaceutical Industry:
(S)-(-)-1,2-Epoxybutane is used as a synthetic building block for the production of α-ethyltryptamines, which are dual dopamine-serotonin releasers. These compounds have potential applications in the treatment of neurological and psychiatric disorders.
Used in Antibiotic Synthesis:
(S)-(-)-1,2-Epoxybutane is used as a starting material to prepare (+)and (?)-homononactic acids. These acids are essential intermediates in the total synthesis of tetranactin, a cyclic antibiotic with potent antibacterial properties.
Used in Chiral Synthesis:
(S)-(-)-1,2-Epoxybutane is used to prepare a chiral phosphorus synthon, which is applicable in the synthesis of phytoprostane B1 type I. (S)-(-)-1,2-Epoxybutane has potential applications in the development of new chiral molecules and pharmaceuticals.
Used in Catalyst Preparation:
(S)-(-)-1,2-Epoxybutane is used to prepare Eu3+-based precatalysts that are applicable in the Mukaiyama Aldol reaction in water. This reaction is an important carbon-carbon bond-forming process in organic synthesis, and the use of (S)-(-)-1,2-Epoxybutane in the preparation of precatalysts can enhance the reaction's efficiency and selectivity.

InChI:InChI=1/C4H8O/c1-2-4-3-5-4/h4H,2-3H2,1H3/t4-/m0/s1

Upstream product

• 106-88-7 ethyloxirane 
• 70379-72-5 (R)-2-acetoxy-1-bromobutane 
• 40348-66-1 (R)-1,2-butanediol 
• 93246-17-4 ((R)-2-Hydroxy-butyl)-trimethyl-ammonium; hydroxide 
• 136656-75-2 (R)-(-)-1-(benzenesulfanyl)-2-butanol 
• 56536-49-3 (2S)-2-chlorobutan-1-ol 
• 51-79-6 urethane 
• 111873-09-7 (2R,3R)-2,3-Bis-benzoyloxy-3-carboxy-propionate((S)-2-hydroxy-butyl)-dimethyl-sulfonium; 
• 72952-75-1 (S)-1,3-butanediol acetonide 
• 93246-18-5 ((S)-2-Hydroxy-butyl)-trimethyl-ammonium; hydroxide 
• 108269-46-1 (2R)-2-chlorobutan-1-ol 
• 143-33-9 sodium cyanide 
• 917-61-3 sodium isocyanate 
• 145021-04-1 (R)-1-tert-Butylsulfanyl-butan-2-ol 

Downstream Products

• 93246-19-6 (R)-2-(3,5-Bisphenyl)-2-(2-hydroxybutyl)-1,3-dithiane 
• 13552-21-1 (R)(-)-1-aminobutan-2-ol 
• 198561-27-2 (R)-3-hydroxypentanenitrile 
• 179396-48-6 (R)-1-(4-methoxyphenyl)butan-2-ol 
• 4476-77-1 (S)-3-tetradecanol 
• 176165-02-9 (S)-1-(2-Methoxymethoxy-phenylamino)-butan-2-ol 
• 1038436-21-3 (S)-(+)-1-[2-(benzyloxy)-5-tert-butylphenoxy]butan-2-ol 
• 1233934-52-5 (1R,2R)-2-ethylcyclopropyl phenyl sulfone 
• 1241048-46-3 ethyl (1S,2R)-1-benzyl-2-ethylcyclopropanecarboxylate 

Relevant academic research and scientific papers

Enantioselective Resolution Copolymerization of Racemic Epoxides and Anhydrides: Efficient Approach for Stereoregular Polyesters and Chiral Epoxides

Herein we report an efficient strategy for preparing isotactic polyesters and chiral epoxides via enantioselective resolution copolymerization of racemic terminal epoxides with anhydrides, mediated by enantiopure bimetallic complexes in conjunction with a nucleophilic cocatalyst. The chirality of both the axial linker and the diamine backbones of the ligand are responsible for the chiral induction of this kinetic resolution copolymerization process. The catalyst systems exhibit exceptional levels of enantioselectivity with a kinetic resolution coefficient exceeding 300 for various racemic epoxides, affording highly isotactic copolymers (selectivity factors of more than 300) with a completely alternating structure and low polydispersity index. Most of the produced isotactic polyesters are typical semicrystalline materials with melting temperatures in the range from 77 to 160 °C.

Aromatic Donor-Acceptor Interaction-Based Co(III)-salen Self-Assemblies and Their Applications in Asymmetric Ring Opening of Epoxides

Aromatic donor-acceptor interaction as the driving force to assemble cooperative catalysts is described. Pyrene/naphthalenediimide functionalized Co(III)-salen complexes self-assembled into bimetallic catalysts through aromatic donor-acceptor interactions and showed high catalytic activity and selectivity in the asymmetric ring opening of various epoxides. Control experiments, nuclear magnetic resonance (NMR) spectroscopy titrations, mass spectrometry measurement, and X-ray crystal structure analysis confirmed that the catalysts assembled based on the aromatic donor-acceptor interaction, which can be a valuable noncovalent interaction in supramolecular catalyst development.

OXYSTEROLS AND METHODS OF USE THEREOF

Compounds are provided according to Formula (I): and pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof; wherein R2, R3, R4, R5, and and R6 are as defined herein. Compounds of the present invention are contemplated useful for the prevention and treatment of a variety of conditions.

Application of homochiral alkylated organic cages as chiral stationary phases for molecular separations by capillary gas chromatography

Molecular organic cage compounds have attracted considerable attention due to their potential applications in gas storage, catalysis, chemical sensing, molecular separations, etc. In this study, a homochiral pentyl cage compound was synthesized from a condensation reaction of (S,S)-1,2-pentyl-1,2-diaminoethane and 1,3,5-triformylbenzene. The imine-linked pentyl cage diluted with a polysiloxane (OV-1701) was explored as a novel stationary phase for high-resolution gas chromatographic separation of organic compounds. Some positional isomers were baseline separated on the pentyl cage-coated capillary column. In particular, various types of enantiomers including chiral alcohols, esters, ethers and epoxides can be resolved without derivatization on the pentyl cage-coated capillary column. The reproducibility of the pentyl cage-coated capillary column for separation was investigated using nitrochlorobenzene and styrene oxide as analytes. The results indicate that the column has good stability and separation reproducibility after being repeatedly used. This work demonstrates that molecular organic cage compounds could become a novel class of chiral separation media in the near future.

Azidolysis of epoxides catalysed by the halohydrin dehalogenase from Arthrobacter sp. AD2 and a mutant with enhanced enantioselectivity: an (S)-selective HHDH

Halohydrin dehalogenase from Arthrobacter sp. AD2 catalysed azidolysis of epoxides with high regioselectivity and low to moderate (S)-enantioselectivity (E?=?1–16). Mutation of the asparagine 178 to alanine (N178A) showed increased enantioselectivity towards styrene oxide derivatives and glycidyl ethers. Conversion of aromatic epoxides was catalysed by HheA-N178A with complete enantioselectivity, however the regioselectivity was reduced. As a result of the enzyme-catalysed reaction, enantiomerically pure (S)-β-azido alcohols and (R)-α-azido alcohols (ee???99%) were obtained.

Chiral oligomers of spiro-salencobalt(III)X for catalytic asymmetric cycloaddition of epoxides with CO2

Several new chiral oligomers of spiro-salenCo(III)X (spiro = 1.1′-spirobiindane-7.7′-diol) complexes have been designed, synthesized, and characterized by nuclear magnetic resonance (NMR), infrared (IR), and elemental analyses, in which, the chiral spiro moieties are first introduced into a scaffold of chiral salenCo catalysts. They were used to catalyze the asymmetric cycloaddition of epoxides with carbon dioxide. Under very mild reaction conditions, a kinetic resolution of racemic epoxides with CO2 was smoothly initiated by these chiral oligomer catalysts with good enantioselectivities, which can be attributed to the match effect between chiral backbones of salen and spiro. High stability and easy recyclability are their major advantages.

Asymmetric hydrolytic kinetic resolution with recyclable polymeric Co(iii)-salen complexes: A practical strategy in the preparation of (S)-metoprolol, (S)-toliprolol and (S)-alprenolol: Computational rationale for enantioselectivity

A series of chiral polymeric Co(iii)-salen complexes based on a number of achiral and chiral linkers were synthesized and their catalytic performances were assessed in the asymmetric hydrolytic kinetic resolution of terminal epoxides. The effects of the linker were judiciously studied and it was found that in the case of the chiral BINOL-based polymeric salen complex 1, there was an enrichment in catalyst reactivity and enantioselectivity of the unreacted epoxide, particularly in the case of short as well as long chain aliphatic epoxides. Good isolated yields of the unreacted epoxide (up to 46% compared to 50% theoretical yield) along with high enantioselectivity (up to 99%) were obtained in most cases using catalyst 1. Further studies showed that catalyst 1 could retain its catalytic activity for six cycles under the present reaction conditions without any significant loss in activity or enantioselectivity. To show the practical applicability of the above synthesized catalyst we have synthesised some potent chiral β-blockers in moderate yield and high enantioselectivity using complex 1. The DFT (M06-L/6-31+G??//ONIOM(B3LYP/6-31G?:STO-3G)) calculations revealed that the chiral BINOL linker influences the enantioselectivity achieved with Co(iii)-salen complexes. Further, the transition state calculations show that the R-BINOL linker with the (S,S)-Co(iii)-salen complex is energetically preferred over the corresponding S-BINOL linker with the (S,S)-Co(iii)-salen complex for the HKR of 1,2-epoxyhexane. The role of non-covalent C-H?π interactions and steric effects has been discussed to control the HKR reaction of 1,2-epoxyhexane.

Self-assembly approach toward chiral bimetallic catalysts: Bis-urea-functionalized (Salen)cobalt complexes for the hydrolytic kinetic resolution of epoxides

A series of novel bis-urea-functionalized (salen)Co complexes has been developed. The complexes were designed to form self-assembled structures in solution through intermolecular urea-urea hydrogen-bonding interactions. These bis-urea (salen)Co catalysts resulted in rate acceleration (up to 13atimes) in the hydrolytic kinetic resolution (HKR) of rac-epichlorohydrin in THF by facilitating cooperative activation, compared to the monomeric catalyst. In addition, one of the bis-urea (salen)CoIII catalyst efficiently resolves various terminal epoxides even under solvent-free conditions by requiring much shorter reaction time at low catalyst loading (0.03-0.05amol %). A series of kinetic/mechanistic studies demonstrated that the self-association of two (salen)Co units through urea-urea hydrogen bonds was responsible for the observed rate acceleration. The self-assembly study with the bis-urea (salen)Co by FTIR spectroscopy and with the corresponding (salen)Ni complex by 1HaNMR spectroscopy showed that intermolecular hydrogen-bonding interactions exist between the bis-urea scaffolds in THF. This result demonstrates that self-assembly approach by using non-covalent interactions can be an alternative and useful strategy toward the efficient HKR catalysis.

ISOSELECTIVE POLYMERIZATION OF EPOXIDES

The present invention provides novel bimetallic complexes and methods of using the same in the isoselective polymerization of epoxides. The invention also provides methods of kinetic resolution of epoxides. The invention further provides polyethers with high enantiomeric excess that are useful in applications ranging from consumer goods to materials.

Formation of enantiopure 5-substituted oxazolidinones through enzyme-catalysed kinetic resolution of epoxides

(Chemical Equation Presented) Halohydrin dehalogenase from Agrobacterium radiobacter catalyzed the enantioselective ring opening of terminal epoxides with cyanate as a nucleophile, yielding 5-substituted oxazolidinones in high yields and with high enantiopurity (69-98% ee). This is the first example of the biocatalytic conversion of a range of epoxides to the corresponding oxazolidinones.