24347-54-4

Usage

Uses

Used in Pharmaceutical and Fine Chemicals Industry:
(S)-4-methylpentane-1,2-diol is used as a building block for the synthesis of various pharmaceuticals and fine chemicals. Its chiral nature allows for the creation of specific enantiomers that can exhibit different biological activities, making it a valuable component in drug development.
Used in Polymer and Plastics Industry:
(S)-4-methylpentane-1,2-diol is used as a key component in the manufacturing of polyester resins, polyurethanes, and plasticizers. It serves to increase the flexibility and durability of these polymers, which is crucial for their performance in various applications, such as coatings, adhesives, and elastomers.
Used in Industrial Applications:
(S)-4-methylpentane-1,2-diol is utilized in a wide range of industrial applications due to its ability to improve the properties of polymers. It plays a crucial role in the development of numerous consumer products and industrial goods, contributing to their enhanced performance and durability.

InChI:InChI=1/C6H14O2/c1-5(2)3-6(8)4-7/h5-8H,3-4H2,1-2H3

Upstream product

• 926-56-7 4-methyl-1,3-pentadiene 
• 173917-47-0 1-benzyloxy-4-methylpentan-2-ol 
• 691-37-2 4-Methyl-1-pentene 
• 103260-84-0 4,5-diacetoxy-2-methyl-pent-2-ene 
• 13748-90-8 (S)-2-hydroxyl-3,3-dimethylbutyric acid 
• 87760-51-8 4-methylpentane-1,2-diol 
• 61-90-5 L-leucine 
• 10303-64-7 2-hydroxy-4-methylpentanoic acid 
• 179052-80-3 2-acetoxy-1-benzyloxy-4-methylpentane 
• 179052-72-3 2-acetoxy-4-methylpentan-1-ol 
• 204253-44-1 (S)-1-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-4-methyl-pentan-2-ol 
• 1015693-25-0 Acetic acid (S)-1-acetoxymethyl-3-methyl-butyl ester 
• 132513-54-3 (S)-2-Hydroxy-4-methyl-pentanoic acid butyl ester 
• 17392-84-6 methyl (2S)-2-hydroxy-4-methylpentanoate 

Downstream Products

• 23850-78-4 4-methyl-1,2-epoxypentane 
• 204253-44-1 (S)-1-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-4-methyl-pentan-2-ol 
• 111221-87-5 2-hydroxy-4-methylpentyl-p-toluenesulfonate 

Relevant academic research and scientific papers

Fast synthesis of complex enantiopure heterocyclic scaffolds by a tandem sequence of simple transformations on α-hydroxyaldehydes

Two tandems are faster than one! Properly sequenced reactions initiated by the Petasis aminoalcohol synthesis from boronic acids, diallylamine, and α-hydroxyaldehydes, including free aldoses, leads to rapid construction of complex enantiopure structures (see scheme). Copyright

Site-selective catalysis: Toward a regiodivergent resolution of 1,2-diols

This paper demonstrates that the secondary hydroxyl can be functionalized in preference to the primary hydroxyl of a 1,2-diol. The site selectivity is achieved by using an enantioselective organic catalyst that is able to bond to the diol reversibly and covalently. The reaction has been parlayed into a divergent kinetic resolution on a racemic mixture, providing access to highly enantioenriched secondary-protected 1,2-diols in a single synthetic step.

Synthesis of new chiral ionic liquids from α-hydroxycarboxylic acids

New functionalized optically active N-methylimidazolium ionic liquids with an asymmetric center at the β-position to the imdazole ring were synthesized as bromide salts from optically active α-hydroxycarboxylic acids. The bromide anions were exchanged by carboxylate anions with Amberlite IRA 400 ionic exchange resin.

Osmium tetroxide in poly(ethylene glycol) (PEG): A recyclable reaction medium for rapid asymmetric dihydroxylation under Sharpless conditions

PEG (400) has been used as a recyclable and rapid reaction medium for the asymmetric dihydroxylation of olefins; Sharpless ligand is efficiently recovered and recycled with good enantioselectivity.

N-(α-chloroalkyloxycarbonyl)pyrrolidines as a source of oxygenated d1- reagents

Reaction of the N-(α-chloroalkyloxycarbonyl)pyrrolidines 1 with lithium powder and a catalytic amount of 4,4'-di-tertbutylbiphenyl (DTBB, 2.5 mol-%) in the presence of different electrophiles [iBuCHO, tBuCHO, PhCHO, Et2CO, (CH2)5CO, PhCOMe, Ph2CO, MeaSiCl], in THF at temperatures ranging between -78 and -60°C leads after hydrolysis with water, to the expected functionalized carbamates 2. Deprotection of compounds 2, derived from carbonyl compounds, with lithium hydroxide in a mixture of ethanol and water at 80°C affords the corresponding 1,2-diols 3.

Solid-phase synthesis of peptidomimetic oligomers with a phosphodiesterase backbone

An unnatural biopolymer is described in which amino acid side-chains are presented along a negatively charged phosphodiester backbone. For this purpose, a series of phosphoramidite monomers was prepared from chiral 1,2-diols. These were efficiently converted into oligomers using standard coupling conditions on an automated DNA synthesizer.

Preparation of optically active α-Silylcarbonyl compounds using asymmetric alkylation of α-Silylacetic esters and asymmetric metal-carbene insertion into the Si-H bond.

Substituted α-silylacetic esters have been prepared in good yields and with reasonable diastereoselectivities by three different routes. The first two involved alkylation of the parent α-silylacetic ester enolates, with the chiral auxiliaries being present either on silicon or on the ester function. The third route involving asymmetric insertion of metal-carbenoids into the Si-H band was found to afford better diastereoselectivities, using pantolactane as chiral auxiliary.

N-(chloromethyloxycarbonyl)pyrrolidine as a source of the HOCH2- synthon

The reaction of N-(chloromethyloxycarbonyl)pyrrolidine (1) with lithium powder and a catalytic amount of DTBB (2.5 mol %) in the presence of different electrophiles [Me3SiCl, Bu(i)CHO, Bu(t)CHO, PhCHO, Et2CO, (CH2)5CO, PhCOMe, Ph2CO] in THF at -78°C leads, after hydrolysis with water, to the expected functionalised carbamates 2. Deprotection of the acetophenone derivative 2g with DIBALH at THF reflux yields, after hydrolysis, the corresponding 1,2-diol 3g.

Kinetic resolution of 2-acylated-1,2-diols by lipase-catalyzed enantiomer selective acylation

Enantiomer selectivity of lipase catalyzed acylation of 2-acylated 1,2-diols was studied. First, acylation of 2-acetoxyheptan-1-ol rac-3b with vinyl acetate was investigated by varying the enzymes and the solvent, showing the highest enantiomer selectivity by using lipase from Pseudomonas fluorescens (PfL) in hexane-vinyl acetate (VA). We have found varying or even reversed enantiomer selectivity for different secondary acyl moieties in 2-acyloxyheptan-1-ols rac-3bA-F. Next, all six possible types of enantiomer selective biotransformations (hydrolysis of diacetate and the two kinds of monoacetetes; acylation of diol and the two kinds of monoacetates) were compared on two model diols rac-4b,d. Among the transformations investigated, acetylation of secondary monoacetates rac-3b,d showed the highest enantiomer selectivity. Finally, PfL catalyzed acetylations of several 2-acetylated 1,2-diols rac-3a-g were investigated under our optimum conditions.

Synthesis of propane-2,3-diol combinatorial monomers

Base catalyzed reaction of heterocyclic bases with R-(+)-glycidol gives heteroaryl-propane-2,3-diols which are functionalized to the 3-O-dimethoxytrityl-2-O-phosphoramidites. A dimethoxytrityl-glycidol is reacted with alkyl or aryl Grignard reagents and then phosphitylated to yield 1-O-dimethoxytrityl-2-phosphoramidites. These compounds can be used for combinatorial oligomer synthesis.