(2S,4S)-5-((tert-butyldiphenylsilyl)oxy)-2-methoxy-4-methylpentanal

Base Information

• Chemical Name: (2S,4S)-5-((tert-butyldiphenylsilyl)oxy)-2-methoxy-4-methylpentanal
• CAS No.: 136262-60-7
• Molecular Formula: C₂₃H₃₂O₃Si
• Molecular Weight: 384.591
• Mol file: 136262-60-7.mol

Synonyms:(2S,4S)-5-((tert-butyldiphenylsilyl)oxy)-2-methoxy-4-methylpentanal

Chemical Property of (2S,4S)-5-((tert-butyldiphenylsilyl)oxy)-2-methoxy-4-methylpentanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S)-5-((tert-butyldiphenylsilyl)oxy)-2-methoxy-4-methylpentanal

There total 16 articles about (2S,4S)-5-((tert-butyldiphenylsilyl)oxy)-2-methoxy-4-methylpentanal 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: 80.0%

(2S,4S)-5-((tert-butyldiphenylsilyl)oxy)-2-methoxy-4-methylpentan-1-ol → (2S,4S)-5-((tert-butyldiphenylsilyl)oxy)-2-methoxy-4-methylpentanal (136262-60-7)

Guidance literature:

With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.ejmech.2017.03.082

Reference yield:

7-(tert-butyl-diphenyl-silanyloxy)-4-methoxy-6-methyl-heptane-2,3-diol → (2S,4S)-5-((tert-butyldiphenylsilyl)oxy)-2-methoxy-4-methylpentanal (136262-60-7)

Guidance literature:

With sodium periodate; In acetone; at 20 ℃; for 2.5h;

DOI:10.1021/ol062642i

Reference yield:

tert-butyl-(4-methoxy-2-methyl-but-3-enyloxy)-diphenyl-silane → (2S,4S)-5-((tert-butyldiphenylsilyl)oxy)-2-methoxy-4-methylpentanal (136262-60-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 4.37 mg / aq. HCl / tetrahydrofuran; CH₂Cl₂ / 3 h / 20 °C

2: 96 percent / (S,S)-chiral titanium complex / diethyl ether; tetrahydrofuran / 5 h / -78 °C

3: 97 percent / KH / tetrahydrofuran / 0 - 20 °C

4: 98 percent / [1,3-Mes₂-(N₂C₃H₅)]Cl₂(PCy₃)Ru=CHPh; N-allyl-N-tritylamine; diisopropylethylamine / toluene / 3.5 h / Heating

5: OsO₄; H₂O; N-methylmorpholine N-oxide / acetone / 16 h / 20 °C

6: aq. NaIO₄ / acetone / 2.5 h / 20 °C

With hydrogenchloride; sodium periodate; osmium(VIII) oxide; (S,S)-chiral titanium; [1,3-Mes₂-(N₂C₃H₅)]Cl₂(PCy₃)Ru=CHPh; N-tritylprop-2-en-1-amine; water; potassium hydride; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; acetone; toluene;

DOI:10.1021/ol062642i

upstream raw materials:

(4R,6S)-7-tert-butyldiphenylsilyloxy-4-methoxy-6-methylhept-2-ene

tert-butyl((2S,4R)-4-methoxy-2-methylhept-6-enyloxy)diphenylsilane

(4R,6S)-7-(tert-butyldiphenylsilyloxy)-6-methylhept-1-en-4-ol

(R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal

Downstream raw materials:

(3S,4R,5S,7S)-8-tert-butyldiphenylsilyloxy-4,5-dimethoxy-3,7-dimethyloct-1-ene

(E)-(4S,5R,6S,8S)-9-tert-butyldiphenylsilyloxy-5,6-dimethoxy-2,4,8-trimethylnon-2-enal

(E)-(3S,4S,7S,8R,9S,11S)-12-tert-butyldiphenylsilyloxy-3,8,9-trimethoxy-5,7,11-trimethyldodec-1,5-dien-4-ol

(E)-N-{3-[(1R,2S,4S,5R,6S,9S,10S)-9-tert-butyldimethylsilyloxy-1,4,5,10-tetramethoxy-2,6,8-trimethyldodec-7,11-dienyl]-2,5-dimethoxyphenyl}amine