(3R,4S,6R)-3-hydroxy-4-methyl-5-oxo-6-[(tert-butyl-dimethylsilyl)oxy]-6-phenylhexanal

Base Information

Chemical Name:(3R,4S,6R)-3-hydroxy-4-methyl-5-oxo-6-[(tert-butyl-dimethylsilyl)oxy]-6-phenylhexanal
CAS No.:288374-69-6
Molecular Formula:C₁₉H₃₀O₄Si
Molecular Weight:350.53
Hs Code.:

Synonyms:(3R,4S,6R)-3-hydroxy-4-methyl-5-oxo-6-[(tert-butyl-dimethylsilyl)oxy]-6-phenylhexanal

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Chemical Property of (3R,4S,6R)-3-hydroxy-4-methyl-5-oxo-6-[(tert-butyl-dimethylsilyl)oxy]-6-phenylhexanal

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Technology Process of (3R,4S,6R)-3-hydroxy-4-methyl-5-oxo-6-[(tert-butyl-dimethylsilyl)oxy]-6-phenylhexanal

There total 5 articles about (3R,4S,6R)-3-hydroxy-4-methyl-5-oxo-6-[(tert-butyl-dimethylsilyl)oxy]-6-phenylhexanal 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: 87.0%

: 288374-68-5
(3R,4S,6R)-1,1-diethoxy-3-hydroxy-4-methyl-5-oxo-6-[(tert-butyl-dimethylsilyl)oxy]-6-phenylhexane

: 288374-69-6
(3R,4S,6R)-3-hydroxy-4-methyl-5-oxo-6-[(tert-butyl-dimethylsilyl)oxy]-6-phenylhexanal

Guidance literature:: With water; trichloroacetic acid; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1016/S0040-4020(00)00255-6

Reference yield:

: 20698-91-3
(R)-methyl mandelate

: 288374-69-6
(3R,4S,6R)-3-hydroxy-4-methyl-5-oxo-6-[(tert-butyl-dimethylsilyl)oxy]-6-phenylhexanal

Guidance literature:: Multi-step reaction with 5 steps

1.1: Me₃Al / benzene; hexane / 0 - 20 °C

1.2: 93 percent / benzene / 20 °C

2.1: 93 percent / Et₃N / CH₂Cl₂ / 3 h / 0 °C

3.1: 94 percent / tetrahydrofuran; diethyl ether / 5 h / 0 °C

4.1: diisopropylethylamine; dibutylboron triflate / CH₂Cl₂ / -78 - 0 °C

4.2: 65 percent / CH₂Cl₂ / -78 - 0 °C

5.1: 87 percent / trichloroacetic acid; water / CH₂Cl₂ / 1 h / 20 °C

With di-n-butylboryl trifluoromethanesulfonate; water; trimethylaluminum; triethylamine; N-ethyl-N,N-diisopropylamine; trichloroacetic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; benzene; 1.1: Metallation / 1.2: Substitution / 2.1: silylation / 3.1: Grignard reaction / 4.1: Addition / 4.2: Condensation / 5.1: Hydrolysis;
DOI:10.1016/S0040-4020(00)00255-6

Reference yield:

: 288374-65-2
(R)-(-)-N-methyl-N-methoxy(2-hydroxy-2-phenyl)acetamide

: 288374-69-6
(3R,4S,6R)-3-hydroxy-4-methyl-5-oxo-6-[(tert-butyl-dimethylsilyl)oxy]-6-phenylhexanal

Guidance literature:: Multi-step reaction with 4 steps

1.1: 93 percent / Et₃N / CH₂Cl₂ / 3 h / 0 °C

2.1: 94 percent / tetrahydrofuran; diethyl ether / 5 h / 0 °C

3.1: diisopropylethylamine; dibutylboron triflate / CH₂Cl₂ / -78 - 0 °C

3.2: 65 percent / CH₂Cl₂ / -78 - 0 °C

4.1: 87 percent / trichloroacetic acid; water / CH₂Cl₂ / 1 h / 20 °C

With di-n-butylboryl trifluoromethanesulfonate; water; triethylamine; N-ethyl-N,N-diisopropylamine; trichloroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: silylation / 2.1: Grignard reaction / 3.1: Addition / 3.2: Condensation / 4.1: Hydrolysis;
DOI:10.1016/S0040-4020(00)00255-6