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

Base Information

Chemical Name:(2S,3R)-3-[(2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2,3-bis-trimethylsilanyloxy-butyl]-oxirane-2-carbaldehyde
CAS No.:360580-57-0
Molecular Formula:C₂₉H₄₆O₅Si₃
Molecular Weight:558.938
Hs Code.:

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

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

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

There total 6 articles about (2S,3R)-3-[(2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2,3-bis-trimethylsilanyloxy-butyl]-oxirane-2-carbaldehyde 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: 90.0%

: 360580-56-9
{(2R,3R)-3-[(2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2,3-bis-trimethylsilanyloxy-butyl]-oxiranyl}-methanol

: 360580-57-0
(2S,3R)-3-[(2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2,3-bis-trimethylsilanyloxy-butyl]-oxirane-2-carbaldehyde

Guidance literature:: With pyridine; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1021/ol016118h

Reference yield:

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

: 360580-57-0
(2S,3R)-3-[(2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2,3-bis-trimethylsilanyloxy-butyl]-oxirane-2-carbaldehyde

Guidance literature:: Multi-step reaction with 4 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

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

Reference yield:

: 533-67-5
2-Deoxy-D-ribose

: 360580-57-0
(2S,3R)-3-[(2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2,3-bis-trimethylsilanyloxy-butyl]-oxirane-2-carbaldehyde

Guidance literature:: Multi-step reaction with 6 steps

1: 92 percent / tetrahydrofuran / 90 °C

2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C

3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating

4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C

5: 73 percent / tBuOOH; D(-)diethyl tartrate; Ti(OiPr)4 / CH₂Cl₂ / 2 h / -20 °C

6: 90 percent / Dess-Martin Periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate; diisobutylaluminium hydride; Dess-Martin periodane; dmap; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol016118h