76639-80-0

Basic information

• Product Name: ((2S,3S)-3-ethyl-2-methyloxiran-2-yl)methanol
• Synonyms: ((2S,3S)-3-ethyl-2-methyloxiran-2-yl)methanol
• CAS NO: 76639-80-0
• Molecular Weight: 116.16
• Mol File: 76639-80-0.mol

Chemical Properties

• CAS DataBase Reference: ((2S,3S)-3-ethyl-2-methyloxiran-2-yl)methanol(CAS DataBase Reference)
• NIST Chemistry Reference: ((2S,3S)-3-ethyl-2-methyloxiran-2-yl)methanol(76639-80-0)
• EPA Substance Registry System: ((2S,3S)-3-ethyl-2-methyloxiran-2-yl)methanol(76639-80-0)

Safety Data

• Hazardous Substances Data: 76639-80-0(Hazardous Substances Data)

Upstream product

• 16958-19-3 (2E)-2-methyl-2-penten-1-ol 
• 1617-40-9 ethyl (E)-2-methyl-2-pentenoate 
• 623-36-9 (E)-2-methylpent-2-enal 
• 1610-29-3 2-methyl-pent-2-en-1-ol 
• 98485-38-2 3-ethyl-2-methyloxirane-2-carbaldehyde 
• 131829-44-2 (2R,3S)-3-ethyl-2-methyl-oxirane-2-carbaldehyde 
• 16958-20-6 (Z)-2-methyl-2-penten-1-ol 

Downstream Products

• 124871-88-1 (2S,3R)-3-(4-methoxybenzyloxy)-2-methylpentane-1,2-diol 
• 87641-44-9 (2S,3R,4S,5R)-1,3,4-trihydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylheptane 
• 124871-91-6 (2S,3R)-3-(4-methoxybenzyloxy)-2-methoxymethoxy-2-methylpentan-1-ol 
• 125325-86-2 (2R,3R)-3-(4-methoxybenzyloxy)-2-methoxymethoxy-2-methylpentanal 
• 124871-93-8 (2E,4S,5R)-2,4-dimethyl-5-(4-methoxybenzyloxy)-4-methoxymethoxyhept-2-en-1-ol 
• 124871-95-0 (2S,3R,4S,5R)-2,4-dimethyl-5-(4-methoxybenzyloxy)-4-methoxymethoxyheptane-1,3-diol 
• 124871-92-7 ethyl (2E,4S,5R)-2,4-dimethyl-5-(4-methoxybenzyloxy)-4-methoxymethoxyhept-2-enoate 
• 124871-94-9 (2S,3R,4S,5R)-2,4-dimethyl-2,3-epoxy-5(4-methoxybenzyloxy)-4-methoxymethoxyheptan-1-ol 
• 124871-94-9 {(2S,3S)-3-[(1R,2R)-2-(4-Methoxy-benzyloxy)-1-methoxymethoxy-1-methyl-butyl]-2-methyl-oxiranyl}-methanol 
• 122358-36-5 Toluene-4-sulfonic acid (4S,5S)-4-methyl-5-(tetrahydro-pyran-2-yloxy)-heptyl ester 
• 72522-40-8 (4R,6S,7S)-7-hydroxy-4,6-dimethyl-3-nonanone 
• 72598-35-7 (-)-serricornin 
• 72522-40-8 (4RS,6SR,7SR)-Serricornin 
• 90074-16-1 (4R,5R)-5-ethyl-4-methyl-2-(4-methoxyphenyl)-1,3-dioxolane-4-carbaldehyde 

Relevant articles and documents

The cinchona primary amine-catalyzed asymmetric epoxidation and hydroperoxidation of α,β-unsaturated carbonyl compounds with hydrogen peroxide

Using cinchona alkaloid-derived primary amines as catalysts and aqueous hydrogen peroxide as the oxidant, we have developed highly enantioselective Weitz-Scheffer-type epoxidation and hydroperoxidation reactions of α,β-unsaturated carbonyl compounds (up to 99.5:0.5 er). In this article, we present our full studies on this family of reactions, employing acyclic enones, 5-15-membered cyclic enones, and α-branched enals as substrates. In addition to an expanded scope, synthetic applications of the products are presented. We also report detailed mechanistic investigations of the catalytic intermediates, structure-activity relationships of the cinchona amine catalyst, and rationalization of the absolute stereoselectivity by NMR spectroscopic studies and DFT calculations.

Catalytic asymmetric epoxidation of α-branched enals

An asymmetric catalytic epoxidation of α-branched, α,β-unsaturated aldehydes is presented. A highly synergistic combination of a primary cinchona-based amine and a chiral phosphoric acid was found to promote the reaction with excellent enantiocontrol for α-monosubstituted and α,β-disubstituted enals.

Exploration of chiral induction on epoxides in lipase-catalyzed epoxidation of alkenes using (2R,3S,4R,5S)-(-)-2,3:4,6-di-O-isopropylidiene-2-keto-l-gulonic acid monohydrate

Epoxidation of alkenes by peracid, generated in situ from (2R,3S,4R,5S)-(-)-2,3:4,6-di-O-isopropylidiene-2-keto-l-gulonic acid monohydrate [(-)-DIKGA] and hydrogen peroxide by lipase catalysis induces chirality on the product epoxides with moderate to good enantioselectivity (35-71%). Alkoxy/aralkyloxy styrenes however did not undergo any epoxidation. (R)-(+)-4-Hydroxy styrene-7,8-oxide was formed and isolated with moderate enantiomeric excess (57%) but was found to have poor stability.

Stereoselective formal total synthesis of (+)-methynolide

(Chemical Equation Presented) A highly stereoselective and convergent formal total synthesis of (+)-methynolide is described. The salient features of this synthesis have been the construction of the C1-C7 and C8-C11fragments via a desymmetrization approach, Sharpless asymmetric epoxidation of an allyl alcohol, respectively, and linkage of both the fragments by Nozaki-Hiyama-Kishi reaction.

Design of optically active hydroxamic acids as ligands in vanadium- catalyzed asymmetric epoxidation

New optically active hydroxamic acids bearing a 1,1'-binaphthyl group were prepared as ligands in a vanadium-catalyzed asymmetric epoxidation. The feature of these hydroxamic acids is a sterically hindered ligand. The asymmetric epoxidation with good selectivity and reactivity can be established by using VO(O-i-Pr)3 (5 mol%) and a small excess amount of ligand (7.5 mol%) with triphenylmethyl hydroperoxide (TrOOH) in toluene at - 20 °C. Disubstituted allyl alcohols were epoxidized more rapidly than mono- or tri-substituted allyl alcohols, and were obtained in good to high enantioselectivities (48 - 94%ee). The transition state based on X-ray crystal structure of 1e is discussed.

A pH Study on the Chiral Ketone Catalyzed Asymmetric Epoxidation of Hydroxyalkenes

A detailed study shows that the chiral ketone catalyzed asymmetric epoxidations of hydroxyalkenes are highly pH dependent. The lower enantioselectivity obtained at low pH is attributed to the substantial contribution of the direct epoxidation by Oxone. At high pH the epoxidation mediated by chiral ketone out-competes the racemic epoxidation, leading to higher enantioselectivity. The effective substrates include allylic alcohol, homoallylic alcohol, and bishomoallylic alcohol. In most cases, over 90% ee was obtained.

Synthesis of (1S,2R,5R)-2-ehyl-1,5-dimethyl-6,8-dioxabicyclo[3.2.1]octane, the aggregation pheromone of male beech bark beetles, Taphrorychus bicolor (Col., Scol.)

The absolute configuration of the new bicyclic acetal 2-ethyl-1,5-dimethyl-6,8-dioxabicyclo[3.2.1]octane (1), identified as an aggregation pheromone of males of the beech bark beetle, Taphrorychus bicolor, was determined by unambiguous synthesis and NMR e

NEW STEREOCONTROLLED APPROACH TO THE INSECT SEX PHEROMONE SERRICORNIN

The (Z)-allylic alcohol 1 was subjected to Sharpless asymmetric epoxidation to give the key intermediate 2.Ring opening of the epoxide 2 afforded the diol 3, which was then converted to serricornin 4, the sex pheromone of the cigarette beetle (Lasioderma serricorne F.) by routine transformations.

Short Enantioselective Approach to a Building Block for Macrolide Syntheses

The protected α,β-dihydroxy aldehyde 2, a key building block for several macrolide antibiotics, has been synthesized from the epoxy alcohol 6.Oxidation furnishes the corresponding aldehyde 7, which is acetalized with ketones in the presence of SnCl4, with

Facile synthesis of (-)-serricornin by means of palladium-catalyzed hydrogenolysis of alkenyloxiranes

Chiral synthesis of (-)-serricornin by using palladium-catalyzed stereoselective hydrogenolysis of the alkenyloxirane to the homoallylic alcohol with formic acid as a key step was carried out.