(E)-4-[(2R,3R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methyl-oxiranyl]-2-methyl-but-2-en-1-ol

Base Information

Chemical Name:(E)-4-[(2R,3R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methyl-oxiranyl]-2-methyl-but-2-en-1-ol
CAS No.:565183-89-3
Molecular Formula:C₂₅H₃₄O₃Si
Molecular Weight:410.629
Hs Code.:

Synonyms:(E)-4-[(2R,3R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methyl-oxiranyl]-2-methyl-but-2-en-1-ol

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Chemical Property of (E)-4-[(2R,3R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methyl-oxiranyl]-2-methyl-but-2-en-1-ol

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Technology Process of (E)-4-[(2R,3R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methyl-oxiranyl]-2-methyl-but-2-en-1-ol

There total 5 articles about (E)-4-[(2R,3R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methyl-oxiranyl]-2-methyl-but-2-en-1-ol 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: 75.0%

: 565183-88-2
(2R,3R)-1-O-tert-butyldiphenylsilyl-2,3-epoxy-3,6-dimethyl-5-hepten-1-ol

: 565183-89-3
(E)-4-[(2R,3R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methyl-oxiranyl]-2-methyl-but-2-en-1-ol

Guidance literature:: (2R,3R)-1-O-tert-butyldiphenylsilyl-2,3-epoxy-3,6-dimethyl-5-hepten-1-ol; With tert.-butylhydroperoxide; selenium(IV) oxide; water; In dichloromethane; at 0 ℃; for 48h;

With sodium tetrahydroborate; In methanol; at 0 ℃; for 1h;
DOI:10.1021/ol034539o

Reference yield:

: 43160-61-8,103606-17-3,43161-23-5
(E)-3,6-dimethyl-2,5-heptadien-1-ol

: 565183-89-3
(E)-4-[(2R,3R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methyl-oxiranyl]-2-methyl-but-2-en-1-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: D-(-)-diisopropyl tartrate; Ti(i-PrO)4; t-BuOOH / 4 Angstroem molecular sieves / CH₂Cl₂; decane / -40 - -18 °C

2.1: imidazole / CH₂Cl₂ / 0.5 h / 0 °C

3.1: SeO₂; t-BuOOH; H₂O / CH₂Cl₂ / 48 h / 0 °C

3.2: 75 percent / NaBH₄ / methanol / 1 h / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; selenium(IV) oxide; water; D-(-)-diisopropyl tartrate; 4 A molecular sieve; In decane; dichloromethane; 1.1: Sharpless asymmetric epoxidation;
DOI:10.1021/ol034539o

Reference yield:

: 24529-80-4
(E)-1-O-acetyl-4-chloro-3-methyl-2-buten-1-ol

: 565183-89-3
(E)-4-[(2R,3R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methyl-oxiranyl]-2-methyl-but-2-en-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 75 percent / MeOH; aq. Na₂CO₃ / 6 h / 0 °C

2.1: Mg; I₂ / tetrahydrofuran / 1 h / 20 °C

2.2: 87 percent / CuI / tetrahydrofuran; diethyl ether / 3 h / -50 °C

3.1: D-(-)-diisopropyl tartrate; Ti(i-PrO)4; t-BuOOH / 4 Angstroem molecular sieves / CH₂Cl₂; decane / -40 - -18 °C

4.1: imidazole / CH₂Cl₂ / 0.5 h / 0 °C

5.1: SeO₂; t-BuOOH; H₂O / CH₂Cl₂ / 48 h / 0 °C

5.2: 75 percent / NaBH₄ / methanol / 1 h / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; selenium(IV) oxide; water; iodine; sodium carbonate; D-(-)-diisopropyl tartrate; magnesium; 4 A molecular sieve; In tetrahydrofuran; decane; dichloromethane; 3.1: Sharpless asymmetric epoxidation;
DOI:10.1021/ol034539o