15071-36-0

Usage

Uses

Used in the Synthesis of Phytosterols:
[S,(+)]-2,3-Dimethyl-1-butanol is used as a key intermediate in the synthesis of phytosterols, which are a class of steroid compounds similar to cholesterol that occur naturally in plants. Phytosterols have various health benefits, such as reducing cholesterol levels and providing anti-inflammatory and antioxidant properties. The use of (S)-2,3-Dimethyl-1-butanol in the synthesis process allows for the production of these beneficial compounds, which can be utilized in the pharmaceutical, nutraceutical, and food industries.
Used in the Pharmaceutical Industry:
In the pharmaceutical industry, [S,(+)]-2,3-Dimethyl-1-butanol can be used as a building block for the development of new drugs, particularly those targeting specific receptors or enzymes. Its chiral nature and unique structural features make it a valuable component in the design and synthesis of novel therapeutic agents.
Used in the Flavor and Fragrance Industry:
Due to its distinct chemical structure, [S,(+)]-2,3-Dimethyl-1-butanol can be used as a component in the creation of various flavors and fragrances. Its unique scent and taste properties can contribute to the development of new and innovative products in the flavor and fragrance market.
Used in the Chemical Industry:
[S,(+)]-2,3-Dimethyl-1-butanol can also be utilized in the chemical industry for the production of various chemicals and materials. Its versatile structure allows it to be used as a starting material or a building block in the synthesis of a wide range of compounds, including specialty chemicals, polymers, and other materials with specific properties and applications.

Upstream product

• 15071-34-8 (2S)-2,3-Dimethylbutanoic acid 
• 122778-53-4 (S)-2,3-Dimethyl-butyric acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 64-17-5 ethanol 
• 92340-78-8 ethyl ester of/the/ (+)(S)-methyl-isopropyl-acetic acid 
• 108-88-3 toluene 
• 83803-31-0 (2S)-1-tert-butyldipheylsilyoxy-2,3-dimethylbutane 
• 601-79-6 isopropylmalonic acid 
• 1015422-42-0 (S)-2,3,N-trimethyl-N-[(S)-1-methyl-2-oxo-2-phenylethyl]-N-butyramide 
• 145589-03-3 (S)-4-benzyl-3-(3-methylbutanoyl)oxazolidin-2-one 
• 49642-48-0 (R)-2,3-dimethylbutanal 
• 15019-26-8 (R)-2,3-dimethyl-butyric acid methyl ester 
• 111042-70-7 (1R,3R,4S)-8-phenyl-p-menthan-3-yl (2R)-2-hydroxymethyl-3-methylbutyrate 
• 145589-03-3 (R)-4-benzyl-3-(3-methylbutyryl)oxazolidin-2-one 
• 1432629-51-0 (R)-4-benzyl-3-((R)-2,3-dimethylbutanoyl)oxazolidin-2-one 

Downstream Products

• 15164-29-1 (S)-1-bromo-2,3-dimethyl-butane 
• 71412-26-5 (+)(S)-(2.3-dimethyl-butyl)-acetate 
• 111042-72-9 (2S)-2,3-dimethylbutyl (S)-3,3,3-trifluoro-2-methoxy-2-phenylpropionate 
• 1900-53-4 campesteryl acetate 
• 1380442-17-0 (S)-(+)-(2,3-dimethylbutyl)triphenylphosphonium iodide 
• 137143-33-0 (S)-2,3-dimethylbutyl 4-methylbenzenesulfonate 
• 139403-46-6 6β-methoxy-3α,5-cyclo-24-α-methyl-5α-cholestane 
• 1900-53-4 24-methylcholest-5-en-3β-yl acetate 
• 15139-34-1 Toluene-4-sulfonic acid (S)-1-[(S)-1-((3S,8S,9S,10R,13S,14S,17R)-3-methoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-ethyl]-3,4-dimethyl-pentyl ester 
• 68702-73-8 (R)-(-)-(2,3-dimethylbutyl)triphenylphosphonium iodide 
• 152912-17-9 (R)-2,3-dimethylbutyl 4-methylbenzenesulfonate 

Relevant academic research and scientific papers

Radical deoxygenation of tertiary alcohols via trifluoroacetates

Trifluoroacetates of tertiary alcohols undergo deoxygenation by Ph 2SiH2 in the presence of (tBuO)2 in excellent yields of the deoxy products without affecting the stereochemistry at β-carbon.

Chiral Synthesis via Organoboranes. 4. Synthetic Utility of Boronic Esters of Essentially 100percent Optical Purity. Synthesis of Homologated Boronic Acids and Esters of Very High Enantiomeric Purities

2-Alkyl-1,3,2-dioxaborinanes, R*BO2(CH2)3, of essentially 100percent optical purity, prepared by the asymmetric hydroboration of readily available prochiral olefins with subsequent removal of the chiral auxiliary, can be homologated to α-chloroalkyl derivatives, R*CHClBO2(CH2)3, of essentially 100percent ee by reaction with LiCHCl2.The intermediates R*CHClBO2(CH2)3 are smoothly reduced with KIPBH to give the corresponding one-carbon-homologated boronic esters R*CH2BO2(CH2)3 in very high optical purity.The operation can be repeated to produce R*CH2CH2BO2(CH2)3 etc.Consequently, it is now possible to synthesize a wide variety of optically active boronic esters, not available by direct asymmetric hydroboration, either (+) or (-), in essentially 100percent ee, and to convert these into synthetically valuable compounds.

A crystalline, internally-coordinated chloroborane for asymmetric hydroboration

Asymmetric hydroboration is an important method in the preparation of enantiomerically-enriched compounds that are necessary in many areas of chemistry. Here is reported the preparation of a unique chiral chloroborane-internal ether complex and its applic

Enantioselective catalytic approach to the C23–C28 subunit of 24α-methyl steroids

Enantioselective synthesis of C23–C28 subunit of campestane steroids based on catalytic methods is reported. The synthesis was started from (S)-2-isopropyl-4-nitrobutan-1-ol, which is easily accessible by the reaction between isovaleraldehyde and nitroethylene catalyzed by only 2% of (S)-trimethylsilyldiphenylprolinol. Removal of one “extra” carbon from the nitroalcohol was achieved by Ni-catalyzed hydrodecarboxylation of the redox-active ester intermediate. The synthesized C23–C28 fragment was attached to a steroidal core by Julia-Kocienski reaction of a steroidal aldehyde with metallated C23–C28 sulfone. The obtained product of olefination was easily transformed to a precursor of campesterol and (Z)-22-dehydrocampesterol.

Copper-catalyzed enantioselective hydroboration of unactivated 1, 1-disubstituted alkenes

We report an efficient and highly enantioselective hydroboration of aliphatic 1, 1-disubstituted alkenes with pinacolborane using a phosphine-Cu catalyst. The method allows facile preparation of enantiomerically enriched β-chiral alkyl pinacolboronates from a range of 1, 1-disubstituted alkenes with high enantioselectivity up to 99% ee. Unprecedented enantiodiscrimination between the geminal alkyl substituents was observed with functional group compatibility in the hydroboration. Furthermore, a catalyst loading as low as 1 mol % furnished the desired product without a decrease in yield or selectivity, demonstrating its efficiency in gram scale synthesis.

Enantioselective Formal α-Methylation and α-Benzylation of Aldehydes by Means of Photo-organocatalysis

Detailed herein is the photochemical organocatalytic enantioselective α-alkylation of aldehydes with (phenylsulfonyl)alkyl iodides. The chemistry relies on the direct photoexcitation of enamines to trigger the formation of reactive carbon-centered radicals from iodosulfones, while the ground-state chiral enamines provide effective stereochemical control over the radical trapping process. The phenylsulfonyl moiety, acting as a redox auxiliary group, facilitates the generation of radicals. In addition, it can eventually be removed under mild reducing conditions to reveal methyl and benzyl groups.

Rational Design of Thermodynamic and Kinetic Binding Profiles by Optimizing Surface Water Networks Coating Protein-Bound Ligands

A previously studied congeneric series of thermolysin inhibitors addressing the solvent-accessible S2′ pocket with different hydrophobic substituents showed modulations of the surface water layers coating the protein-bound inhibitors. Increasing stabilization of water molecules resulted in an enthalpically more favorable binding signature, overall enhancing affinity. Based on this observation, we optimized the series by designing tailored P2′ substituents to improve and further stabilize the surface water network. MD simulations were applied to predict the putative water pattern around the bound ligands. Subsequently, the inhibitors were synthesized and characterized by high-resolution crystallography, microcalorimetry, and surface plasmon resonance. One of the designed inhibitors established the most pronounced water network of all inhibitors tested so far, composed of several fused water polygons, and showed 50-fold affinity enhancement with respect to the original methylated parent ligand. Notably, the inhibitor forming the most perfect water network also showed significantly prolonged residence time compared to the other tested inhibitors.

Sensing remote chirality: Stereochemical determination of β-, γ-, and δ-chiral carboxylic acids

Determining the absolute stereochemisty of small molecules bearing remote nonfunctionalizable stereocenters is a challenging task. Presented is a solution in which appropriately substituted bis(porphyrin) tweezers are used. Complexation of a suitably derivatized β-, γ-, or δ-chiral carboxylic acid to the tweezer induces a predictable helicity of the bis(porphyrin), which is detected as a bisignate Cotton Effect (ECCD). The sign of the ECCD curve is correlated with the absolute stereochemistry of the substrate based on the derived working mnemonics in a predictable manner.

Synthetic routes to campesterol and dihydrobrassicasterol: A first reported synthesis of the key phytosterol dihydrobrassicasterol

Phytosterols are increasingly used as health supplements in functional foods and are associated with having both positive and negative effects on health. Given this disparity, an investigation of their full individual biological profile is imperative in order to assure food safety. This paper describes the de novo synthesis of pure phytosterols in multigram scale and we report the first synthesis of the key phytosterol dihydrobrassicasterol along with a comparison of routes to campesterol. A detailed spectroscopic analysis is included with full assignment of the 13C NMR spectroscopic data of both compounds, mixtures and their precursors leading to the potential use of NMR spectroscopy as a tool for analysis of these sterol mixtures.

9-Borabicyclo[3.3.2]decanes and the asymmetric hydroboration of 1,1-disubstituted alkenes

The syntheses of the optically pure asymmetric hydroborating agents 1 (a, R = Ph; b, R = TMS) in both enantiomeric forms are reported. These reagents are effective for the hydroboration of cis-, trans- and trisubstituted alkenes. More significantly, they exhibit unprecedented levels of selectivity in the asymmetric hydroboration of 1,1-disubstituted alkenes (28-92% ee), a previously unanswered challenge in the nearly 50 year history of this reagent-controlled process. For example, the hydroboration of α-methylstyrene with 1a produces the corresponding alcohol 6f in 78% ee (cf., Ipc2BH, 5% ee). Suzuki coupling of the intermediate adducts 5 produces the nonracemic products 7 very effectively (50-84%) without loss of optical purity. Copyright