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

Base Information

Chemical Name:ethyl (2S,3R,4R)-5-(tert-butyldiphenylsiloxy)-3-methoxymethoxy-2,4-dimethylpentanoate
CAS No.:630117-31-6
Molecular Formula:C₂₇H₄₀O₅Si
Molecular Weight:472.697
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

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

There total 5 articles about ethyl (2S,3R,4R)-5-(tert-butyldiphenylsiloxy)-3-methoxymethoxy-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: 85.0%

: 630117-25-8
ethyl (2S,3R,4R)-2-bromo-5-(tert-butyldiphenylsiloxy)-3-methoxymethoxy-4-methylpentanoate

: 630117-31-6
ethyl (2S,3R,4R)-5-(tert-butyldiphenylsiloxy)-3-methoxymethoxy-2,4-dimethylpentanoate

: 630117-29-2
ethyl (2R,3R,4R)-5-(tert-butyldiphenylsiloxy)-3-methoxymethoxy-2,4-dimethylpentanoate

Guidance literature:: With triethyl borane; tri-n-butyl-tin hydride; In hexane; toluene; at -78 ℃; for 2h;
DOI:10.1016/j.tetasy.2003.06.005

Reference yield:

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

: 630117-31-6
ethyl (2S,3R,4R)-5-(tert-butyldiphenylsiloxy)-3-methoxymethoxy-2,4-dimethylpentanoate

Guidance literature:: Multi-step reaction with 4 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

3.1: 91 percent / P₂O₅ / CHCl₃ / 3 h / 20 °C

4.1: 82 percent / Mg; 1,2-dibromoethane; Bu₃SnH / Et₃B / CH₂Cl₂; hexane / 15 h / -78 °C

With oxalyl dichloride; tri-n-butyl-tin hydride; phosphorus pentoxide; magnesium; dimethyl sulfoxide; ethylene dibromide; lithium diisopropyl amide; triethyl borane; In tetrahydrofuran; hexane; dichloromethane; chloroform; 1.1: Swern oxidation;
DOI:10.1016/j.tetasy.2003.06.005

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 630117-31-6
ethyl (2S,3R,4R)-5-(tert-butyldiphenylsiloxy)-3-methoxymethoxy-2,4-dimethylpentanoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaH / tetrahydrofuran / 0.75 h / 20 °C

1.2: 74 percent / tetrahydrofuran / 15 h / 20 °C

2.1: 88 percent / (COCl)2; DMSO / CH₂Cl₂ / 0.33 h / -78 °C

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

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

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

4.1: 91 percent / P₂O₅ / CHCl₃ / 3 h / 20 °C

5.1: 82 percent / Mg; 1,2-dibromoethane; Bu₃SnH / Et₃B / CH₂Cl₂; hexane / 15 h / -78 °C

With oxalyl dichloride; tri-n-butyl-tin hydride; phosphorus pentoxide; sodium hydride; magnesium; dimethyl sulfoxide; ethylene dibromide; lithium diisopropyl amide; triethyl borane; In tetrahydrofuran; hexane; dichloromethane; chloroform; 2.1: Swern oxidation;
DOI:10.1016/j.tetasy.2003.06.005