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

Base Information

Chemical Name:(3R,4S,6R)-1,1-diethoxy-3-hydroxy-4-methyl-5-oxo-6-[(tert-butyl-dimethylsilyl)oxy]-6-phenylhexane
CAS No.:288374-68-5
Molecular Formula:C₂₃H₄₀O₅Si
Molecular Weight:424.653
Hs Code.:

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

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Chemical Property of (3R,4S,6R)-1,1-diethoxy-3-hydroxy-4-methyl-5-oxo-6-[(tert-butyl-dimethylsilyl)oxy]-6-phenylhexane

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Technology Process of (3R,4S,6R)-1,1-diethoxy-3-hydroxy-4-methyl-5-oxo-6-[(tert-butyl-dimethylsilyl)oxy]-6-phenylhexane

There total 4 articles about (3R,4S,6R)-1,1-diethoxy-3-hydroxy-4-methyl-5-oxo-6-[(tert-butyl-dimethylsilyl)oxy]-6-phenylhexane 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: 65.0%

: 6367-37-9
3,3-diethoxypropanal

: 288374-67-4
(R)-(+)-(1-tert-butyldimethylsilyloxy-1-phenyl)butan-2-one

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

Guidance literature:: (R)-(+)-(1-tert-butyldimethylsilyloxy-1-phenyl)butan-2-one; With di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 - 0 ℃;

3,3-diethoxypropanal; In dichloromethane; at -78 - 0 ℃;
DOI:10.1016/S0040-4020(00)00255-6

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 4 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

With di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; triethylamine; N-ethyl-N,N-diisopropylamine; 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;
DOI:10.1016/S0040-4020(00)00255-6

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 3 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

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