(2S,5R)-2-tert-butyldimethylsilyloxy-5-hydroxy-6-methyl-1-phenyl-3-heptanone

Base Information

Chemical Name:(2S,5R)-2-tert-butyldimethylsilyloxy-5-hydroxy-6-methyl-1-phenyl-3-heptanone
CAS No.:1213779-31-7
Molecular Formula:C₂₀H₃₄O₃Si
Molecular Weight:350.574
Hs Code.:

Synonyms:(2S,5R)-2-tert-butyldimethylsilyloxy-5-hydroxy-6-methyl-1-phenyl-3-heptanone

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Chemical Property of (2S,5R)-2-tert-butyldimethylsilyloxy-5-hydroxy-6-methyl-1-phenyl-3-heptanone

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Technology Process of (2S,5R)-2-tert-butyldimethylsilyloxy-5-hydroxy-6-methyl-1-phenyl-3-heptanone

There total 3 articles about (2S,5R)-2-tert-butyldimethylsilyloxy-5-hydroxy-6-methyl-1-phenyl-3-heptanone 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:

: 78-84-2
isobutyraldehyde

: (S)-3-tert-butyldimethylsilyloxy-4-phenyl-2-butanone

: (2S,5S)-2-tert-butyldimethylsilyloxy-5-hydroxy-6-methyl-1-phenyl-3-heptanone

: 1213779-31-7
(2S,5R)-2-tert-butyldimethylsilyloxy-5-hydroxy-6-methyl-1-phenyl-3-heptanone

Guidance literature:: (S)-3-tert-butyldimethylsilyloxy-4-phenyl-2-butanone; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -94 ℃; Inert atmosphere;

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

Reference yield:

: C₂₀H₃₃NO₂Si

: (2S,5S)-2-tert-butyldimethylsilyloxy-5-hydroxy-6-methyl-1-phenyl-3-heptanone

: 1213779-31-7
(2S,5R)-2-tert-butyldimethylsilyloxy-5-hydroxy-6-methyl-1-phenyl-3-heptanone

Guidance literature:: Multi-step reaction with 2 steps

1.1: methyllithium / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere

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

2.2: 0.5 h / -94 °C / Inert atmosphere

2.3: 0.5 h / -78 °C / Inert atmosphere

With methyllithium; titanium tetrachloride; In tetrahydrofuran; dichloromethane; 2.1: |Aldol Addition;
DOI:10.1016/j.tet.2014.12.099

Reference yield:

: 905307-55-3
(2S)-2-tert-butyldimethylsilyloxy-N-methoxy-3-methyl-N-methylbutanamide

: (2S,5S)-2-tert-butyldimethylsilyloxy-5-hydroxy-6-methyl-1-phenyl-3-heptanone

: 1213779-31-7
(2S,5R)-2-tert-butyldimethylsilyloxy-5-hydroxy-6-methyl-1-phenyl-3-heptanone

Guidance literature:: Multi-step reaction with 2 steps

1.1: tetrahydrofuran; toluene / 2 h / 0 °C / Inert atmosphere

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

2.2: 0.5 h / -94 °C / Inert atmosphere

2.3: 0.5 h / -78 °C / Inert atmosphere

With titanium tetrachloride; In tetrahydrofuran; dichloromethane; toluene; 2.1: |Aldol Addition;
DOI:10.1016/j.tet.2014.12.099