(2R,4S)-5-[tert-butyl(diphenyl)silyl]oxy-2,4-dimethylpentan-1-ol

Base Information

• Chemical Name: (2R,4S)-5-[tert-butyl(diphenyl)silyl]oxy-2,4-dimethylpentan-1-ol
• CAS No.: 157837-64-4
• Molecular Formula: C₂₃H₃₄O₂Si
• Molecular Weight: 370.607
• DSSTox Substance ID: DTXSID301147167
• Nikkaji Number: J2.446.664G
• Mol file: 157837-64-4.mol

Synonyms:DTXSID301147167;157837-64-4;(2R,4S)-5-[[(1,1-Dimethylethyl)diphenylsilyl]oxy]-2,4-dimethyl-1-pentanol

Chemical Property of (2R,4S)-5-[tert-butyl(diphenyl)silyl]oxy-2,4-dimethylpentan-1-ol

Chemical Property:

• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 9
• Exact Mass: 370.232806857
• Heavy Atom Count: 26
• Complexity: 374

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC(C)CO[Si](C1=CC=CC=C1)(C2=CC=CC=C2)C(C)(C)C)CO
• Isomeric SMILES: C[C@H](C[C@H](C)CO[Si](C1=CC=CC=C1)(C2=CC=CC=C2)C(C)(C)C)CO

Technology Process of (2R,4S)-5-[tert-butyl(diphenyl)silyl]oxy-2,4-dimethylpentan-1-ol

There total 22 articles about (2R,4S)-5-[tert-butyl(diphenyl)silyl]oxy-2,4-dimethylpentan-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: 100.0%

(2R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-2,4-dimethyl-pentanoic acid methyl ester (157837-63-3) → (2R,4S)-5-{[tert-butyl(diphenyl)silyl]oxy}-2,4-dimethylpentan-1-ol (157837-64-4)

Guidance literature:

With diisobutylaluminium hydride;

DOI:10.1021/ja963066w

Reference yield: 97.0%

(2S,4R)-5-(tert-butyl(dimethyl)silyloxy)-2,4-dimethyl-1-pentanol (147782-80-7) + tert-butylchlorodiphenylsilane (58479-61-1) → (2R,4S)-5-{[tert-butyl(diphenyl)silyl]oxy}-2,4-dimethylpentan-1-ol (157837-64-4)

Guidance literature:

(2S,4R)-5-(tert-butyl(dimethyl)silyloxy)-2,4-dimethyl-1-pentanol; tert-butylchlorodiphenylsilane; With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20 ℃;

With pyridinium p-toluenesulfonate; In ethanol; at 50 ℃; for 7h;

DOI:10.1021/ol049356w

Reference yield: 93.0%

C23H32O2Si → (2R,4S)-5-{[tert-butyl(diphenyl)silyl]oxy}-2,4-dimethylpentan-1-ol (157837-64-4) + (2S,4S)-5-((tert-butyldiphenylsilyl)oxy)-2,4-dimethylpentan-1-ol (638188-59-7)

Guidance literature:

With hydrogen; irridium catalyst; In dichloromethane; at 25 ℃; for 4h; under 38002.6 Torr;

DOI:10.1021/ol070298z

upstream raw materials:

(2R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-2,4-dimethyl-pentanoic acid methyl ester

(2S,4R)-5-(tert-butyl(dimethyl)silyloxy)-2,4-dimethyl-1-pentanol

tert-butylchlorodiphenylsilane

C₁₃H₃₀SiO₂SiC₁₆H₁₈

Downstream raw materials:

(2R,4S)-5-{[tert-butyl(diphenyl)silyl]oxy}-2,4-dimethylpentanal

C₂₆H₃₈OSi

Carbonic acid (S)-1-[(1R,3S)-4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-5-(4-methoxy-benzyloxy)-4-methyl-pent-2-ynyl ester methyl ester

tert-butyl-((2S,4R)-2,4-dimethylhex-5-enyloxy)diphenylsilane