107127-75-3

Basic information

• Product Name: (S)-2-methyl-2-<2-(phenylmethoxy)ethyl>oxirane
• Synonyms: (S)-2-methyl-2-<2-(phenylmethoxy)ethyl>oxirane
• CAS NO: 107127-75-3
• Molecular Weight: 192.258
• Mol File: 107127-75-3.mol

Chemical Properties

• CAS DataBase Reference: (S)-2-methyl-2-<2-(phenylmethoxy)ethyl>oxirane(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-methyl-2-<2-(phenylmethoxy)ethyl>oxirane(107127-75-3)
• EPA Substance Registry System: (S)-2-methyl-2-<2-(phenylmethoxy)ethyl>oxirane(107127-75-3)

Safety Data

• Hazardous Substances Data: 107127-75-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(S)-2-methyl-2-<2-(phenylmethoxy)ethyl>oxirane is utilized as a reagent in organic synthesis, taking advantage of its epoxide functionality to facilitate a range of chemical reactions and the formation of new compounds.
Used in Pharmaceutical Production:
In the pharmaceutical industry, (S)-2-methyl-2-<2-(phenylmethoxy)ethyl>oxirane serves as an intermediate in the synthesis of various drugs. Its unique structure allows for the creation of complex molecular architectures that can exhibit specific therapeutic effects.
Used in Agrochemicals:
(S)-2-methyl-2-<2-(phenylmethoxy)ethyl>oxirane is also employed as an intermediate in the production of agrochemicals, such as pesticides and herbicides. Its reactivity and structural properties enable the development of effective compounds for agricultural applications.

Upstream product

• 6236-09-5 (S)-citramalic acid 
• 93239-42-0 (R)-4-methyl-4-(trichloromethyl)-2-oxetanone 
• 58558-53-5 (((3-methylbut-3-en-1-yl)oxy)methyl)benzene 
• 100-39-0 benzyl bromide 
• 763-32-6 2-methyl-1-buten-4-ol 
• 60299-29-8 (S)-(-)-2-Methylbutane-1,2,4-triol 
• 131700-28-2 (S)-2,2,4-trimethyl-4-<2-(phenylmethoxy)ethyl>-1,3-dioxolane 
• 131700-29-3 (S)-2-methyl-4-(2-phenylmethoxy)butane-1,2-diol 
• 38574-61-7 (R)-2-hydroxy-2-methyl-butan-1,4-dioic acid dimethyl ester 
• 64018-43-5 2-[(4S)-2,2,4-trimethyl-1,3-dioxolan-4-yl]ethanol 
• 131700-30-6 (S)-2-hydroxy-2-methyl-4-(2-phenylmethoxy)butyl methanesulphonate 

Downstream Products

• 281200-24-6 (R)-4-(2',5'-dimethoxyphenyl)-3-hydroxy-3-methylbutanal 
• 126680-16-8 1-O-benzyl-3-methyl non-5-yn-3,9-diol 
• 1160112-24-2 C₁₂H₁₈O₄ 
• 70238-41-4 (E)-4-(benzyloxy)-2-methylbut-2-en-1-ol 
• 113522-74-0 4-(benzyloxy)-2-methylenebutan-1-ol 

Relevant articles and documents

Synthesis of Primary gem-Dihydroperoxides and Their Peroxycarbenium [3 + 2] Cycloaddition Reactions with Alkenes

It is long known that dihydroperoxidation of aliphatic aldehydes is extremely difficult and normally stops halfway at the hydroxyhydroperoxide stage. This strange phenomenon now has been explored, and a highly effective protocol for conversion of aliphatic aldehydes into gem-dihydroperoxides has been developed. Silyl protection of primary gem-dihydroperoxides, which is also a challenge due to unexpected based-induced decomposition, was achieved using 2,6-lutidine as the base. The silyl-protected gem-dihydroperoxides were then examined in a peroxycarbenium [3 + 2] cycloaddition reaction with alkenes for the first time. Aromatic substrates normally reacted smoothly, affording the expected 1,2-dioxolanes smoothly. Aliphatic aldehydes generally failed to yield 1,2-dioxolane. In all cases, unexpected formation of either a chlorohydrin or a 1,2-dichloride (with Cl atoms derived from TiCl4) depending on the alkene employed was observed, which displays some so far unknown facets of the cycloaddition and helped to gain many mechanistic insights.

Pigments of Fungi. LIX - Synthesis of (1S,3S)- and (1R,3R)-austrocortilutein and (1S,3S)-austrocortirubin from citramalic acid

The naturally occurring tetrahydroanthraquinone (1S,3S)-austrocortilutein (1) is synthesized for the first time in enantiomerically pure form by Diels-Alder cycloaddition between the functionalized butadiene derivative (8) and the chiral 1,3-dihydroxy-1,2,3,4-tetrahydro-5,8-naphthoquinone (9), the latter being derived from (R)-citramalic acid (3). The natural products (1S,3S)-austrocortirubin (2) and (1R,3R)-austrocortilutein (5) were also prepared for the first time by using the same strategy. CSIRO 2000.

Enantioselective hydrolysis of functionalized 2,2-disubstituted oxiranes with bacterial epoxide hydrolases

The biohydrolysis of 2,2-disubstituted oxiranes bearing various oxygen functional groups was investigated using the epoxide hydrolase activity of 11 bacterial strains. The results show that the activity and the selectivity strongly depend on the substrate structure and the biocatalyst. Whereas substrates possessing free hydroxyl groups were not transformed, their analogs, protected as ethers, were well accepted. This allowed the convenient modulation of the enantioselectivity by proper choice of the ether group according to size and polarity. It was found that the distance of the ether-oxygen to the stereogenic quaternary carbon center of the oxirane ring had a profound influence on the enantioselectivity, and several oxiranes were resolved with good to excellent selectivities. The enantiomerically enriched epoxides and vicinal diols thus obtained contain a useful 'synthetic handle' in their side chain, which allows their use as building blocks in asymmetric synthesis.

Pigments of Fungi, Part 16. Synthesis of Methyl (R)-(+)-Tetrahydro-2-methyl-5-oxo-2-furanacetate and its (S)-(-)-Antipode, Chiroptical References for Detatrmination of the Absolute Stereochemistry of Fungal Pre-anthraquinones.

The (R)- and (S)-butanolides 7 and 9 are synthesised via asymmetric epoxidation from geraniol; the (R)-butanolide 7 is also obtained from (S)-citramalic acid.The butanolides 7 and 9 are valuable reference compounds for the determination of absolute stereochemistry in fungal and plant pre-anthraquinones.

Regioselective Opening of Simple Epoxides with Diisopropylamine Trihydrofluoride

Treatment of benzyl ether derivatives of simple aliphatic epoxy alcohols with diisopropylamine trihydrofluoride gave mixtures of the corresponding fluorohydrins in good yields.Steric hindrance is a major factor in determining the regioselectivity of epoxide opening, although electronic effects cannot be ignored.Electronic effects are more dominant with pyridine polyhydrofluoride.