(2R,3R,5S)-5-(tert-butyldiphenylsilyl)-2,3-(oxiranyl)hexan-1-ol

Base Information

• Chemical Name: (2R,3R,5S)-5-(tert-butyldiphenylsilyl)-2,3-(oxiranyl)hexan-1-ol
• CAS No.: 328114-40-5
• Molecular Formula: C₂₂H₃₀O₃Si
• Molecular Weight: 370.564
• Mol file: 328114-40-5.mol

Synonyms:(2R,3R,5S)-5-(tert-butyldiphenylsilyl)-2,3-(oxiranyl)hexan-1-ol

Chemical Property of (2R,3R,5S)-5-(tert-butyldiphenylsilyl)-2,3-(oxiranyl)hexan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,5S)-5-(tert-butyldiphenylsilyl)-2,3-(oxiranyl)hexan-1-ol

There total 7 articles about (2R,3R,5S)-5-(tert-butyldiphenylsilyl)-2,3-(oxiranyl)hexan-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: 90.0%

(2E,5S)-5-[(tert-butyldiphenylsilyl)oxy]hex-2-en-1-ol (378750-00-6) → (2R,3R,5S)-5-(tert-butyldiphenylsilyl)-2,3-(oxiranyl)hexan-1-ol (328114-40-5)

Guidance literature:

With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate; In dichloromethane; toluene; at -30 ℃;

DOI:10.1021/ja011364+

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (2R,3R,5S)-5-(tert-butyldiphenylsilyl)-2,3-(oxiranyl)hexan-1-ol (328114-40-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: imidazole / CH₂Cl₂ / 0 °C

1.2: 95 percent / CH₂Cl₂ / 25 °C

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

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

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

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

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate; diisobutylaluminium hydride; 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+

Reference yield:

ethyl (E,5S)-5-{[tert-butyl(diphenyl)silyl]oxy}-2-hexenoate (378749-99-6) → (2R,3R,5S)-5-(tert-butyldiphenylsilyl)-2,3-(oxiranyl)hexan-1-ol (328114-40-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / DIBALH / CH₂Cl₂; toluene / -20 - 25 °C

2: 90 percent / (D)-(-)-diethyl tartrate; Ti(OiPr)4; tert-butylhydroperoxide / CH₂Cl₂; toluene / -30 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate; diisobutylaluminium hydride; In dichloromethane; toluene; 2: Sharpless epoxidation;

DOI:10.1021/ja011364+

upstream raw materials:

(2E,5S)-5-[(tert-butyldiphenylsilyl)oxy]hex-2-en-1-ol

tert-butylchlorodiphenylsilane

methyl (3S)-3-{[tert-butyl(diphenyl)silyl]oxy}butanoate

(3S)-3-{[tert-butyl(diphenyl)silyl]oxy}butanal

Downstream raw materials:

(3R,4R,6S)-6-(tert-butyldiphenylsilyl)-3,4-(oxiranyl)hept-1-ene

2-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxy)-6-[((1E,3E)-2-penta-1,3-dienyl)-[1,3]dithian-2-ylmethyl]-benzoic acid (R)-1-methyl-2-((2R,3R)-3-vinyl-oxiranyl)-ethyl ester

C₄₃H₅₆O₅S₂Si₂

4-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-6-[((1E,3E)-2-penta-1,3-dienyl)-[1,3]dithian-2-ylmethyl]-benzoic acid (R)-1-methyl-2-((2R,3R)-3-vinyl-oxiranyl)-ethyl ester