55123-01-8

Usage

Uses

Used in Pharmaceutical Industry:
(2S)-2-(1-Methylethyl)oxirane is used as a reactive intermediate for the synthesis of various pharmaceuticals and organic compounds.
Used in Pesticide Industry:
(2S)-2-(1-Methylethyl)oxirane is used as a reactive intermediate in the manufacture of pesticides.
Used in Flavoring and Fragrance Industry:
(2S)-2-(1-Methylethyl)oxirane is used as a reactive intermediate in the production of flavoring agents and fragrances.
Used in Adhesives, Coatings, and Plastics Industry:
(2S)-2-(1-Methylethyl)oxirane is used in the production of epoxide resins, which are widely utilized in the production of adhesives, coatings, and plastics.
Safety Note:
Isopropyl epoxide is considered to have low toxicity, but it should be handled with care due to its potential to irritate the skin and respiratory system.

Upstream product

• 1438-14-8 2-isopropyloxirane 
• 24347-56-6 (S)-3-methylbutane-1,2-diol 
• 72-18-4 L-valine 
• 17407-55-5 (S)-2-Hydroxy-3-methylbutanoic acid 
• 24347-63-5 methyl (S)-2-hydroxy-3-methylbutanoate 
• 563-45-1 3-Methyl-1-butene 
• 140388-27-8 (R)-2-chloro-3-methylbutan-1-ol 
• 204686-68-0 Toluene-4-sulfonic acid (S)-3-methyl-2-(tetrahydro-pyran-2-yloxy)-butyl ester 
• 204686-66-8 methyl (2S)-3-methyl-2-(tetrahydro-2H-pyran-2-yloxy)butanoate 
• 204686-67-9 (2S)-3-methyl-2-(tetrahydropyran-2-yloxy)butan-1-ol 
• 204686-71-5 (S)-2-Isopropyl-1,4-dioxa-spiro[4.5]decane 
• 90211-82-8 (2S)-1-tosyloxy-3-methylbutan-2-ol 

Downstream Products

• 90211-85-1 (24R)-6β-methoxy-22-phenylsulfonyl-24-hydroxy-3α,5α-cyclocholestane 
• 160069-23-8 (S)-1-(N,N-dibenzylamino)-3-methyl-2-butanol 
• 15272-24-9 edulitine 
• 159973-38-3 (+)-(2'R)-3-(2'-hydroxy-3'-methylbutyl)-2,4,8-trimethoxyquinoline 
• 1416148-66-7 (S)-3-mesyloxy-4-methyl-1-phenylpentane 
• 1416148-68-9 (S)-3-mesyloxy-4-methyl-1-phenylpentane 
• 27460-26-0 24(R)-Hydroxycholesterol 

Relevant academic research and scientific papers

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.

Comparative molecular field analysis of fenoterol derivatives interacting with an agonist-stabilized form of the β2-adrenergic receptor

The β2-adrenergic receptor (β2-AR) agonist [3H]-(R,R′)-methoxyfenoterol was employed as the marker ligand in displacement studies measuring the binding affinities (Ki values) of the stereoisomers of a series of 4′-methoxyfenoterol analogs in which the length of the alkyl substituent at α′ position was varied from 0 to 3 carbon atoms. The binding affinities of the compounds were additionally determined using the inverse agonist [3H]-CGP-12177 as the marker ligand and the ability of the compounds to stimulate cAMP accumulation, measured as EC50 values, were determined in HEK293 cells expressing the β2-AR. The data indicate that the highest binding affinities and functional activities were produced by methyl and ethyl substituents at the α′ position. The results also indicate that the Ki values obtained using [3H]-(R,R′)-methoxyfenoterol as the marker ligand modeled the EC50 values obtained from cAMP stimulation better than the data obtained using [3H]-CGP-12177 as the marker ligand. The data from this study was combined with data from previous studies and processed using the Comparative Molecular Field Analysis approach to produce a CoMFA model reflecting the binding to the β2-AR conformation probed by [3H]-(R,R′)-4′-methoxyfenoterol. The CoMFA model of the agonist-stabilized β2-AR suggests that the binding of the fenoterol analogs to an agonist-stabilized conformation of the β2-AR is governed to a greater extend by steric effects than binding to the [3H]-CGP-12177-stabilized conformation(s) in which electrostatic interactions play a more predominate role.

Cyclopropenone catalyzed substitution of alcohols with mesylate ion

The cyclopropenone catalyzed nucleophilic substitution of alcohols by methanesulfonate ion with inversion of configuration is described. This work provides an alternative to the Mitsunobu reaction that avoids the use of azodicarboxylates and generation of hydrazine and phosphine oxide byproducts. This transformation is shown to be compatible with a range of functionality. A cyclopropenone scavenge strategy is demonstrated to aid purification.

Enantioselective Synthesis and Absolute Configuration of (R)-(+)-Lunacridine and (S)-(+)-Lunacrine

(R)-(-)-Lunacridine 1 has been synthesized in 97.3percent e.e. using a chiron approach through L-valine and D-mannitol as the starting compounds to corroborate its absolute configuration.The key intermediate (S)-1,2-epoxy-3-methylbutane 11 was synthesized from (L)-valine (3 -> -> 11) and a (D)-mannitol derivative (12 -> -> 11) via functional group manipulation.The epoxide 11 was reacted with lithiated 2,4,8-trimethoxyquinoline 17 and the resulting product 18 was selectively deprotected at the 2-position followed by N-methylation of 19 to give 1.In an alternative strategy 11 was transformed into the THP-acid 23 through the chiral lactone 20.Condensation of 23 with substituted methyl anthranilate gave the amide 24 which on cyclisation, methylation and deprotection steps sequentially afforded 1.

Stereoselective Synthesis of Squalamine Dessulfate

Squalamine dessulfate (24R) and the unnatural product squalamine dessulfate (24S) have been synthesized from stigmasterol.The key step is establishing the C24 stereochemistry is attachment of the sidechain at C22 using either (2R)- or (2S)-1,2-epoxy-3-met

A Stereoselective Synthesis and a Convenient Synthesis of Optically Pure (24 R)- and (24 S)-24-hydroxycholesterols

A new stereoselective synthesis of optically pure (24 S)-24-hydroxycholesterol (cerebrosterol) and (24 R)-24-hydroxycholesterol, using D- and L-valines as chiral sources, as well as a convenient synthesis, are described.