ethyl (2S,3R,4R)-2-bromo-5-(tert-butyldiphenylsiloxy)-3-hydroxy-2,4-dimethylpentanoate

Base Information

Chemical Name:ethyl (2S,3R,4R)-2-bromo-5-(tert-butyldiphenylsiloxy)-3-hydroxy-2,4-dimethylpentanoate
CAS No.:625109-60-6
Molecular Formula:C₂₅H₃₅BrO₄Si
Molecular Weight:507.54
Hs Code.:

Synonyms:ethyl (2S,3R,4R)-2-bromo-5-(tert-butyldiphenylsiloxy)-3-hydroxy-2,4-dimethylpentanoate

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Chemical Property of ethyl (2S,3R,4R)-2-bromo-5-(tert-butyldiphenylsiloxy)-3-hydroxy-2,4-dimethylpentanoate

Chemical Property:

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Technology Process of ethyl (2S,3R,4R)-2-bromo-5-(tert-butyldiphenylsiloxy)-3-hydroxy-2,4-dimethylpentanoate

There total 4 articles about ethyl (2S,3R,4R)-2-bromo-5-(tert-butyldiphenylsiloxy)-3-hydroxy-2,4-dimethylpentanoate 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:

: 17360-25-7,32013-47-1,68005-71-0
N-(p-toluenesulfonyl)-L-valine

: 123284-89-9
(+/-)-2-methyl-3-[(tert-butyldiphenylsilyl)oxy]propanal

: 153645-08-0
2-bromo-1-ethoxy-2-methyl-1-trimethylsilyoxyethene

: 625109-58-2
ethyl (2S,3R,4S)-2-bromo-5-(tert-butyldiphenylsiloxy)-3-hydroxy-2,4-dimethylpentanoate

: 625109-60-6
ethyl (2S,3R,4R)-2-bromo-5-(tert-butyldiphenylsiloxy)-3-hydroxy-2,4-dimethylpentanoate

Guidance literature:: N-(p-toluenesulfonyl)-L-valine; With borane-THF; In tetrahydrofuran; dichloromethane; at 0 - 20 ℃; for 1h;

(+/-)-2-methyl-3-[(tert-butyldiphenylsilyl)oxy]propanal; 2-bromo-1-ethoxy-2-methyl-1-trimethylsilyoxyethene; In tetrahydrofuran; dichloromethane; at -78 ℃; for 3h;
DOI:10.1021/jo034901c

Reference yield:

: 123284-89-9
(+/-)-2-methyl-3-[(tert-butyldiphenylsilyl)oxy]propanal

: 535-11-5,41978-69-2
Ethyl 2-bromopropionate

: ethyl (2R,3S,4S)-2-bromo-5-(tert-butyldiphenylsiloxy)-3-hydroxy-4-methylpentanoate

: 625109-58-2
ethyl (2S,3R,4S)-2-bromo-5-(tert-butyldiphenylsiloxy)-3-hydroxy-2,4-dimethylpentanoate

: ethyl (2R,3S,4R)-2-bromo-5-(tert-butyldiphenylsiloxy)-3-hydroxy-4-methylpentanoate

: 625109-60-6
ethyl (2S,3R,4R)-2-bromo-5-(tert-butyldiphenylsiloxy)-3-hydroxy-2,4-dimethylpentanoate

Guidance literature:: Ethyl 2-bromopropionate; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.25h;

With chloro-trimethyl-silane; In tetrahydrofuran; at -78 - 20 ℃;

(+/-)-2-methyl-3-[(tert-butyldiphenylsilyl)oxy]propanal; With N-(p-toluenesulfonyl)-L-valine; borane-THF; In dichloromethane; at -78 ℃; for 3h; Further byproducts given. Title compound not separated from byproducts;
DOI:10.1016/j.tetasy.2003.06.005

Reference yield:

: 129029-85-2
(2RS)-3-(tert-butyldiphenylsilyloxy)-2-methylpropanol

: 625109-60-6
ethyl (2S,3R,4R)-2-bromo-5-(tert-butyldiphenylsiloxy)-3-hydroxy-2,4-dimethylpentanoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 88 percent / (COCl)2; DMSO / CH₂Cl₂ / 0.33 h / -78 °C

2.1: LDA / tetrahydrofuran / 0.25 h / -78 °C

2.2: Me₃SiCl / tetrahydrofuran / -78 - 20 °C

2.3: N-p-tosyl-(R)-valine; BH₃*THF / CH₂Cl₂ / 3 h / -78 °C

With oxalyl dichloride; dimethyl sulfoxide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; 1.1: Swern oxidation;
DOI:10.1016/j.tetasy.2003.06.005