(E)-7-((2S,3S)-3-Benzyloxymethyl-3-methyl-oxiranyl)-1-cyclopropyl-5-methyl-hept-4-en-1-one

Base Information

Chemical Name:(E)-7-((2S,3S)-3-Benzyloxymethyl-3-methyl-oxiranyl)-1-cyclopropyl-5-methyl-hept-4-en-1-one
CAS No.:714230-56-5
Molecular Formula:C₂₂H₃₀O₃
Molecular Weight:342.478
Hs Code.:

Synonyms:(E)-7-((2S,3S)-3-Benzyloxymethyl-3-methyl-oxiranyl)-1-cyclopropyl-5-methyl-hept-4-en-1-one

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Chemical Property of (E)-7-((2S,3S)-3-Benzyloxymethyl-3-methyl-oxiranyl)-1-cyclopropyl-5-methyl-hept-4-en-1-one

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Technology Process of (E)-7-((2S,3S)-3-Benzyloxymethyl-3-methyl-oxiranyl)-1-cyclopropyl-5-methyl-hept-4-en-1-one

There total 4 articles about (E)-7-((2S,3S)-3-Benzyloxymethyl-3-methyl-oxiranyl)-1-cyclopropyl-5-methyl-hept-4-en-1-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 100-39-0
benzyl bromide

: 714230-55-4
(4E,8E)-1-Cyclopropyl-10-hydroxy-5,9-dimethyl-deca-4,8-dien-1-one

: 714230-56-5
(E)-7-((2S,3S)-3-Benzyloxymethyl-3-methyl-oxiranyl)-1-cyclopropyl-5-methyl-hept-4-en-1-one

: (E)-7-((2R,3R)-3-Benzyloxymethyl-3-methyl-oxiranyl)-1-cyclopropyl-5-methyl-hept-4-en-1-one

Guidance literature:: (4E,8E)-1-Cyclopropyl-10-hydroxy-5,9-dimethyl-deca-4,8-dien-1-one; With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; molecular sieve; calcium hydride; In dichloromethane; toluene; at -40 - -20 ℃; for 4h;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; for 2h; Title compound not separated from byproducts;
DOI:10.1021/ol049311v

Reference yield:

: 765-43-5
Cyclopropyl methyl ketone

: 714230-56-5
(E)-7-((2S,3S)-3-Benzyloxymethyl-3-methyl-oxiranyl)-1-cyclopropyl-5-methyl-hept-4-en-1-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium diisopropylamide / tetrahydrofuran / 0.5 h / -78 °C

1.2: 52 percent / tetrahydrofuran / -78 - 20 °C

2.1: 56 percent / SeO₂; tert-butyl hydroperoxide / CH₂Cl₂ / 0 - 20 °C

3.1: L-(+)-diethyl tartrate; Ti(OiPr)4; tert-butyl hydroperoxide / CaH₂; molecular sieves / toluene; CH₂Cl₂ / 4 h / -40 - -20 °C

3.2: sodium hydride; tetra-n-butylammmonium iodide / tetrahydrofuran; various solvent(s) / 2 h

With titanium(IV) isopropylate; tert.-butylhydroperoxide; selenium(IV) oxide; diethyl (2R,3R)-tartrate; lithium diisopropyl amide; molecular sieve; calcium hydride; In tetrahydrofuran; dichloromethane; toluene; 3.1: Sharpless epoxidation;
DOI:10.1021/ol049311v

Reference yield:

: 82859-38-9
(2E)-1-iodo-3,7-dimethylocta-2,6-diene

: 714230-56-5
(E)-7-((2S,3S)-3-Benzyloxymethyl-3-methyl-oxiranyl)-1-cyclopropyl-5-methyl-hept-4-en-1-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium diisopropylamide / tetrahydrofuran / 0.5 h / -78 °C

1.2: 52 percent / tetrahydrofuran / -78 - 20 °C

2.1: 56 percent / SeO₂; tert-butyl hydroperoxide / CH₂Cl₂ / 0 - 20 °C

3.1: L-(+)-diethyl tartrate; Ti(OiPr)4; tert-butyl hydroperoxide / CaH₂; molecular sieves / toluene; CH₂Cl₂ / 4 h / -40 - -20 °C

3.2: sodium hydride; tetra-n-butylammmonium iodide / tetrahydrofuran; various solvent(s) / 2 h

With titanium(IV) isopropylate; tert.-butylhydroperoxide; selenium(IV) oxide; diethyl (2R,3R)-tartrate; lithium diisopropyl amide; molecular sieve; calcium hydride; In tetrahydrofuran; dichloromethane; toluene; 3.1: Sharpless epoxidation;
DOI:10.1021/ol049311v