(2R,3R)-3-{(2R)-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}propyl}oxirane-2-methanol

Base Information

Chemical Name:(2R,3R)-3-{(2R)-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}propyl}oxirane-2-methanol
CAS No.:303044-41-9
Molecular Formula:C₂₂H₃₀O₃Si
Molecular Weight:370.564
Hs Code.:

Synonyms:(2R,3R)-3-{(2R)-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}propyl}oxirane-2-methanol

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Chemical Property of (2R,3R)-3-{(2R)-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}propyl}oxirane-2-methanol

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Technology Process of (2R,3R)-3-{(2R)-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}propyl}oxirane-2-methanol

There total 10 articles about (2R,3R)-3-{(2R)-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}propyl}oxirane-2-methanol 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%

: 303044-40-8
(2E,5R)-5-{[(1,1-dimethylethyl)diphenylsilyl]oxy}hex-2-en-1-ol

: 303044-41-9
(2R,3R)-3-{(2R)-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}propyl}oxirane-2-methanol

Guidance literature:: With titanium(IV) isopropylate; tert.-butylhydroperoxide; (+)-Weinsaeure-diethylester; In dichloromethane; toluene; at -30 ℃; for 12h;
DOI:10.1021/ja011364+

Reference yield:

: 183310-90-9
(R)-3-(tert-butyl-diphenyl-silanyloxy)-butyraldehyde

: 303044-41-9
(2R,3R)-3-{(2R)-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}propyl}oxirane-2-methanol

Guidance literature:: Multi-step reaction with 3 steps

1: 95 percent / LiCl; DIPEA / acetonitrile / 12 h / 25 °C

2: 96 percent / DIBALH / CH₂Cl₂; toluene / 5 h / -20 - 25 °C

3: 90 percent / (D)-(+)-diethyl tartrate; Ti(OiPr)4; tert-butylhydroperoxide / CH₂Cl₂; toluene / 12 h / -30 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; diisobutylaluminium hydride; (+)-Weinsaeure-diethylester; N-ethyl-N,N-diisopropylamine; lithium chloride; In dichloromethane; toluene; acetonitrile; 1: Wadsworth-Horner-Emmons homologation / 3: Sharpless epoxidation;
DOI:10.1021/ja011364+

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 303044-41-9
(2R,3R)-3-{(2R)-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}propyl}oxirane-2-methanol

Guidance literature:: Multi-step reaction with 5 steps

1.1: imidazole / CH₂Cl₂ / 0.17 h / 0 °C

1.2: 97 percent / CH₂Cl₂ / 4 h / 25 °C

2.1: 92 percent / DIBALH / toluene / 0.17 h / -78 °C

3.1: 95 percent / LiCl; DIPEA / acetonitrile / 12 h / 25 °C

4.1: 96 percent / DIBALH / CH₂Cl₂; toluene / 5 h / -20 - 25 °C

5.1: 90 percent / (D)-(+)-diethyl tartrate; Ti(OiPr)4; tert-butylhydroperoxide / CH₂Cl₂; toluene / 12 h / -30 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; diisobutylaluminium hydride; (+)-Weinsaeure-diethylester; N-ethyl-N,N-diisopropylamine; lithium chloride; In dichloromethane; toluene; acetonitrile; 3.1: Wadsworth-Horner-Emmons homologation / 5.1: Sharpless epoxidation;
DOI:10.1021/ja011364+