70423-38-0

Usage

Uses

Used in the Synthesis of Pheromones:
(S)-2-Methyl-1,4-butanedanol is used as a key intermediate in the synthesis of sex pheromones for various species, including pine sawflies. Its unique stereochemistry allows for the production of biologically active compounds that can effectively attract and communicate with the target species.
Used in the Chemical Industry:
As a chiral building block, (S)-2-methyl-1,4-butanediol is used in the chemical industry for the synthesis of various pharmaceuticals, agrochemicals, and specialty chemicals. Its specific stereochemistry makes it a valuable component in the development of enantiomerically pure compounds, which are essential for the biological activity and safety of many drugs.
Used in the Flavor and Fragrance Industry:
Due to its unique odor and flavor profile, (S)-2-methyl-1,4-butanediol can be used as a component in the flavor and fragrance industry. It can contribute to the creation of specific scents and tastes in various consumer products, such as perfumes, cosmetics, and the food industry.
Used in the Production of Lubricants and Additives:
(S)-2-Methyl-1,4-butanediol's properties as a secondary alcohol make it suitable for use in the production of lubricants and additives for the automotive and industrial sectors. Its ability to form hydrogen bonds can improve the performance and efficiency of these products.
Used in the Research and Development of New Materials:
The unique stereochemistry and properties of (S)-2-methyl-1,4-butanediol make it an interesting candidate for research and development in the field of new materials. It can be used to explore novel applications in areas such as polymer science, materials engineering, and nanotechnology.

InChI:InChI=1/C5H12O2/c1-5(4-7)2-3-6/h5-7H,2-4H2,1H3/t5-/m0/s1

Upstream product

• 105226-56-0 methyl (3S)-3-methyl-4-oxobutanoate 
• 135137-66-5 ((E)-(S)-4,7-Dimethyl-octa-2,6-dienyl)-benzene 
• 74549-14-7 (E/Z)-4-Acetoxy-2-methyl-2-butenal-dimethylacetal 
• 1283688-39-0 (1R,3S)-2,2-dichloro-3-methylcyclopropanecarboxylic acid 
• 108-05-4 vinyl acetate 
• 2938-98-9 2-methyl-1,4-butandiol 
• 13865-21-9 methyl 3-formyl-2-methylpropionate 
• 132364-45-5 (1E,3R)-N,N-diethyl-3-methyl-4-<(trimethylsilyl)oxy>but-1-enylamine 
• 107650-07-7 (3S)-4,4-dimethoxy-3-methylbutan-1-ol 
• 132364-20-6 (R)-3-Methyl-4-[((E)-propenyl)oxy]-butyraldehyde 
• 120263-03-8 (3R,5R)-5-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-3-methyl-dihydro-furan-2-one 
• 120263-02-7 (4R,5S)-5-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxy)-4-methyl-dihydro-furan-2-one 
• 120263-02-7 4(R)5(R)-4-methyl-5-(1-menthyloxy)-butyrolactone 
• 22644-27-5 (R)-methylsuccinic acid dimethyl ester 

Downstream Products

• 64190-48-3 (S)-3-methyl-4-butanolide 
• 169387-99-9 (S)-2-methyl-4-(tert-butyldiphenylsilyloxy)butanol 
• 173209-00-2 (3S)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-methylbutan-1-ol 
• 956242-57-2 (S)-1-((tert-butyldiphenylsilyl)oxy)-3-methyloctan-4-one 
• 187458-29-3 (2S, 3S)-5-(tert-butyldiphenylsilyloxy)-3-methylpentane-1,2-diol 
• 120329-65-9 (S)-2-methylbutane-1,4-diol dibenzoate 
• 1204312-94-6 C₂₂H₂₉IOSi 
• 1268247-04-6 C₂₉H₃₈O₅Si 
• 1204312-95-7 C₂₉H₃₈O₅Si 
• 1268246-93-0 C₂₃H₂₇F₃O₇ 
• 1268246-94-1 C₃₃H₄₄O₅Si 
• 11076-19-0 bongkrekic acid 
• 1443650-81-4 (2S)-2-methyl-4-(1-phenyl-1H-tetrazole-5-sulfonyl)butan-1-ol 
• 1443650-82-5 (S)-5-(2-methyl-4-(1-phenyl-1H-tetrazol-5-ylsulfonyl)butylthio)-1-phenyl-1H-tetrazole 

Relevant academic research and scientific papers

Synthesis and complete structure determination of a sperm-activating and -attracting factor isolated from the ascidian ascidia sydneiensis

For the complete structure elucidation of an endogenous sperm-activating and -attracting factor isolated from eggs of the ascidian Ascidia sydneiensis (Assydn-SAAF), its two possible diastereomers with respect to C-25 were synthesized. Starting from ergosterol, the characteristic steroid backbone was constructed by using an intramolecular pinacol coupling reaction and stereoselective reduction of a hydroxy ketone as key steps, and the side chain was introduced by Julia-Kocienski olefination. Comparison of the NMR data of the two diastereomers with those of the natural product led to the elucidation of the absolute configuration as 25S; thus the complete structure was determined and the first synthesis of Assydn-SAAF was achieved.

Cobalt versus Osmium: Control of Both trans and cis Selectivity in Construction of the EFG Rings of Pectenotoxin 4

Catalytic oxidative cyclisation reactions have been employed for the synthesis of the E and F rings of the complex natural product target pectenotoxin 4. The choice of metal catalyst (cobalt- or osmium-based) allowed for the formation of THF rings with either trans or cis stereoselectivity. Fragment union using a modified Julia reaction then enabled the synthesis of an advanced synthetic intermediate containing the EF and G rings of the target.

Iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones to chiral diols

We report a protocol for the highly efficient iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones via dynamic kinetic resolution. Using Ir-SpiroPAP (R)-1d as a catalyst, a wide range of chiral diols were prepared in a high yield (80-95%) with a high enantioselectivity (up to 95% ee) under mild reaction conditions. This protocol was used for enantioselective syntheses of (?)-preclamol and a chiral 2,5-disubstituted tetrahydropyran.

Enantioselective Hydroformylation of 1-Alkenes with Commercial Ph-BPE Ligand

A rhodium complex, in conjunction with commercially available Ph-BPE ligand, catalyzes the branch-selective asymmetric hydroformylation of 1-alkenes and rapidly generates α-chiral aldehydes. A wide range of terminal olefins including 1-dodecene were examined, and all delivered high enantioselectivity (up to 98:2 er) as well as good branch:linear ratios (up to 15:1). (Chemical Equation Presented).

Facile synthesis of versatile enantioenriched α-substituted hydroxy esters through a Bronsted acid catalyzed kinetic resolution

An efficient synthesis of enantioenriched α-substituted γ-hydroxy esters via a kinetic resolution event is described. Bulky racemic esters in the presence of a chiral Bronsted acid selectively lactonize to yield a recoverable enantioenriched hydroxy ester and lactone. These esters are highly versatile building blocks that can readily be converted to synthetically useful materials.

Using heteroaryl-lithium reagents as hydroxycarbonyl anion equivalents in conjugate addition reactions with (S, S)-(+)-pseudoephedrine as chiral auxiliary; Enantioselective synthesis of 3-substituted pyrrolidines

We have developed an efficient protocol for carrying out the stereocontrolled formal conjugate addition of hydroxycarbonyl anion equivalents to α,β-unsaturated carboxylic acid derivatives using (S,S)-(+)-pseudoephedrine as chiral auxiliary, making use of the synthetic equivalence between the heteroaryl moieties and the carboxylate group. This protocol has been applied as key step in the enantioselective synthesis of 3-substituted pyrrolidines in which, after removing the chiral auxiliary, the heteroaryl moiety is converted into a carboxylate group followed by reduction and double nucleophilic displacement. Alternatively, the access to the same type of heterocyclic scaffold but with opposite absolute configuration has also been accomplished by making use of the regio- and diastereoselective conjugate addition of organolithium reagents to α,β,γ,δ-unsaturated amides derived from the same chiral auxiliary followed by chiral auxiliary removal, ozonolysis, and reductive amination/intramolecular nucleophilic displacement sequence.

Chiral methyl trans-2,2-dichloro-3-methylcyclopropanecarboxylate upon exposure to thiophenolate nucleophile

Substitution of the β-halogen atoms in methyl (1R,3S)-2,2-dichloro-3- ethylycyclopropanecarboxylate with sodium thiophenolate leads to the di(phenylthio) ester (1RS,3S)-4 as a mixture of diastereomers. The cis-trans isomerisation of methyl (1RS,3S)-3-methyl-2,2-bis(phenylthio)- cyclopropanecarboxylate 4, basic hydrolysis and subsequent crystallization gave the corresponding acid (1R,3S)-5 in high diastereomeric and enantiomeric purity. On the other hand, ring opening of the ester (1RS,3S)-4 under acidic conditions leads to methyl 3-methyl-4,4-di(phenylthio)prop-3-enoate (8) or the chiral S-phenyl thioester methyl (3S)-3-methyl-4-oxo-4-(phenylthio)butanoate (7).ARKAT-USA, Inc.

Direct regiospecific and highly enantioselective intermolecular α-allylic alkylation of aldehydes by a combination of transition-metal and chiral amine catalysts

The first direct intermolecular regiospecific and highly enantioselective α-allylic alkylation of linear aldehydes by a combination of achiral bench-stable Pd0 complexes and simple chiral amines as co-catalysts is disclosed. The co-catalytic asymmetric chemoselective and regiospecific α-allylic alkylation reaction is linked in tandem with in situ reduction to give the corresponding 2-alkyl alcohols with high enantiomeric ratios (up to 98:2 e.r.; e.r.=enantiomeric ratio). It is also an expeditious entry to valuable 2-alkyl substituted hemiacetals, 2-alkyl-butane-1,4-diols, and amines. The concise co-catalytic asymmetric total syntheses of biologically active natural products (e.g., Arundic acid) are disclosed. Go organic! Direct intermolecular regiospecific and highly enantioselective α-allylic alkylation of linear aldehydes by a combination of achiral bench-stable Pd0 complexes and simple chiral amines as co-catalysts is disclosed (see scheme). Copyright

INDANE ESTROGEN RECEPTOR MODULATORS AND USES THEREOF

Described herein are compounds that are estrogen receptor modulators. Also described are pharmaceutical compositions and medicaments that include the compounds described herein, as well as methods of using such estrogen receptor modulators, alone and in combination with other compounds, for treating diseases or conditions that are mediated or dependent upon estrogen receptors.

ESTROGEN RECEPTOR MODULATORS AND USES THEREOF

Described herein are compounds that are estrogen receptor modulators. Also described are pharmaceutical compositions and medicaments that include the compounds described herein, as well as methods of using such estrogen receptor modulators, alone and in combination with other compounds, for treating diseases or conditions that are mediated or dependent upon estrogen receptors.