(1R,4S)-4-((tert-butyldimethylsilyl)oxy)-1-hydroxy-5-methyl-1-phenylhexan-3-one

Base Information

Chemical Name:(1R,4S)-4-((tert-butyldimethylsilyl)oxy)-1-hydroxy-5-methyl-1-phenylhexan-3-one
CAS No.:1213779-37-3
Molecular Formula:C₁₉H₃₂O₃Si
Molecular Weight:336.547
Hs Code.:

Synonyms:(1R,4S)-4-((tert-butyldimethylsilyl)oxy)-1-hydroxy-5-methyl-1-phenylhexan-3-one

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Chemical Property of (1R,4S)-4-((tert-butyldimethylsilyl)oxy)-1-hydroxy-5-methyl-1-phenylhexan-3-one

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Technology Process of (1R,4S)-4-((tert-butyldimethylsilyl)oxy)-1-hydroxy-5-methyl-1-phenylhexan-3-one

There total 12 articles about (1R,4S)-4-((tert-butyldimethylsilyl)oxy)-1-hydroxy-5-methyl-1-phenylhexan-3-one 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:

: 100-52-7
benzaldehyde

: (S)-3-((tert-butyldimethylsilyl)oxy)-4-methylpentan-2-one

: (1S,4S)-4-((tert-butyldimethylsilyl)oxy)-1-hydroxy-5-methyl-1-phenylhexan-3-one

: 1213779-37-3
(1R,4S)-4-((tert-butyldimethylsilyl)oxy)-1-hydroxy-5-methyl-1-phenylhexan-3-one

Guidance literature:: (S)-3-((tert-butyldimethylsilyl)oxy)-4-methylpentan-2-one; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -94 ℃; Inert atmosphere;

benzaldehyde; In dichloromethane; at -78 ℃; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tetlet.2009.12.046

Reference yield:

: C₂₄H₄₇BO₂Si

: 100-52-7
benzaldehyde

: (1S,4S)-4-((tert-butyldimethylsilyl)oxy)-1-hydroxy-5-methyl-1-phenylhexan-3-one

: 1213779-37-3
(1R,4S)-4-((tert-butyldimethylsilyl)oxy)-1-hydroxy-5-methyl-1-phenylhexan-3-one

Guidance literature:: C₂₄H₄₇BO₂Si; benzaldehyde; In diethyl ether; at -78 ℃; for 1h; Inert atmosphere;

With dihydrogen peroxide; In methanol; at 0 ℃; for 1h; Overall yield = 64 %; Overall yield = 54 mg; diastereoselective reaction; Inert atmosphere;
DOI:10.1039/c9ob00358d

Reference yield:

: 24347-63-5
methyl (S)-2-hydroxy-3-methylbutanoate

: (1S,4S)-4-((tert-butyldimethylsilyl)oxy)-1-hydroxy-5-methyl-1-phenylhexan-3-one

: 1213779-37-3
(1R,4S)-4-((tert-butyldimethylsilyl)oxy)-1-hydroxy-5-methyl-1-phenylhexan-3-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 20 °C / Inert atmosphere

2.1: dmap; triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere

3.1: methyllithium / tetrahydrofuran / 1 h / -40 °C / Inert atmosphere

4.1: titanium tetrachloride / dichloromethane / 0.08 h / -94 °C / Inert atmosphere

4.2: 0.5 h / -94 °C / Inert atmosphere

4.3: 0.5 h / -78 °C / Inert atmosphere

With dmap; methyllithium; titanium tetrachloride; triethylamine; In tetrahydrofuran; dichloromethane; 4.1: |Aldol Addition;
DOI:10.1016/j.tet.2014.12.099