(2R,3R)-2-[(2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2,3-bis-trimethylsilanyloxy-butyl]-3-ethyl-oxirane

Base Information

Chemical Name:(2R,3R)-2-[(2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2,3-bis-trimethylsilanyloxy-butyl]-3-ethyl-oxirane
CAS No.:360580-59-2
Molecular Formula:C₃₀H₅₀O₄Si₃
Molecular Weight:558.981
Hs Code.:

Synonyms:(2R,3R)-2-[(2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2,3-bis-trimethylsilanyloxy-butyl]-3-ethyl-oxirane

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Chemical Property of (2R,3R)-2-[(2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2,3-bis-trimethylsilanyloxy-butyl]-3-ethyl-oxirane

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Technology Process of (2R,3R)-2-[(2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2,3-bis-trimethylsilanyloxy-butyl]-3-ethyl-oxirane

There total 8 articles about (2R,3R)-2-[(2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2,3-bis-trimethylsilanyloxy-butyl]-3-ethyl-oxirane 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%

: 360580-58-1
(2R,3R)-2-[(2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2,3-bis-trimethylsilanyloxy-butyl]-3-vinyl-oxirane

: 360580-59-2
(2R,3R)-2-[(2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2,3-bis-trimethylsilanyloxy-butyl]-3-ethyl-oxirane

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethyl acetate; at 20 ℃; for 1.5h;
DOI:10.1021/ol016118h

Reference yield:

: (E)-(5S,6R)-7-(tert-Butyl-diphenyl-silanyloxy)-5,6-dihydroxy-hept-2-enoic acid ethyl ester

: 360580-59-2
(2R,3R)-2-[(2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2,3-bis-trimethylsilanyloxy-butyl]-3-ethyl-oxirane

Guidance literature:: Multi-step reaction with 6 steps

1: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating

2: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C

3: 73 percent / tBuOOH; D(-)diethyl tartrate; Ti(OiPr)4 / CH₂Cl₂ / 2 h / -20 °C

4: 90 percent / Dess-Martin Periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C

5: 55 percent / n-butyllithium / tetrahydrofuran; various solvent(s) / 6 h / 20 °C

6: 75 percent / H₂ / Pd/C / ethyl acetate / 1.5 h / 20 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; diethyl (2S,3S)-tartrate; hydrogen; diisobutylaluminium hydride; Dess-Martin periodane; dmap; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate;
DOI:10.1021/ol016118h

Reference yield:

: (E)-(5S,6R)-7-(tert-Butyl-diphenyl-silanyloxy)-5,6-bis-trimethylsilanyloxy-hept-2-en-1-ol

: 360580-59-2
(2R,3R)-2-[(2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2,3-bis-trimethylsilanyloxy-butyl]-3-ethyl-oxirane

Guidance literature:: Multi-step reaction with 4 steps

1: 73 percent / tBuOOH; D(-)diethyl tartrate; Ti(OiPr)4 / CH₂Cl₂ / 2 h / -20 °C

2: 90 percent / Dess-Martin Periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C

3: 55 percent / n-butyllithium / tetrahydrofuran; various solvent(s) / 6 h / 20 °C

4: 75 percent / H₂ / Pd/C / ethyl acetate / 1.5 h / 20 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; diethyl (2S,3S)-tartrate; hydrogen; Dess-Martin periodane; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate;
DOI:10.1021/ol016118h