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

Base Information

Chemical Name:ethyl (2S,3R,4R)-2-bromo-5-(tert-butyldiphenylsiloxy)-3-methoxymethoxy-4-methylpentanoate
CAS No.:630117-25-8
Molecular Formula:C₂₇H₃₉BrO₅Si
Molecular Weight:551.593
Hs Code.:

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

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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)-2-bromo-5-(tert-butyldiphenylsiloxy)-3-methoxymethoxy-4-methylpentanoate

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

There total 4 articles about ethyl (2S,3R,4R)-2-bromo-5-(tert-butyldiphenylsiloxy)-3-methoxymethoxy-4-methylpentanoate 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: 91.0%

: 109-87-5
Dimethoxymethane

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

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

Guidance literature:: With phosphorus pentoxide; In chloroform; at 20 ℃; for 3h;
DOI:10.1016/j.tetasy.2003.06.005

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 3 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

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

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 2 steps

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

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

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

2.1: 91 percent / P₂O₅ / CHCl₃ / 3 h / 20 °C

With phosphorus pentoxide; lithium diisopropyl amide; In tetrahydrofuran; chloroform;
DOI:10.1016/j.tetasy.2003.06.005