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

Base Information

Chemical Name:ethyl (2R,3R,4S)-3-(tert-butyldimethylsiloxy)-5-(tert-butyldiphenylsiloxy)-2,4-dimethylpentanoate
CAS No.:625109-64-0
Molecular Formula:C₃₁H₅₀O₄Si₂
Molecular Weight:542.907
Hs Code.:

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

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

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

There total 7 articles about ethyl (2R,3R,4S)-3-(tert-butyldimethylsiloxy)-5-(tert-butyldiphenylsiloxy)-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: 93.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 625109-63-9
ethyl (2R,3R,4S)-5-(tert-butyldiphenylsiloxy)-3-hydroxy-2,4-dimethylpentanoate

: 625109-64-0
ethyl (2R,3R,4S)-3-(tert-butyldimethylsiloxy)-5-(tert-butyldiphenylsiloxy)-2,4-dimethylpentanoate

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1021/jo034901c

Reference yield:

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

: 625109-64-0
ethyl (2R,3R,4S)-3-(tert-butyldimethylsiloxy)-5-(tert-butyldiphenylsiloxy)-2,4-dimethylpentanoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 88 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

2.1: BH₃*THF / CH₂Cl₂; tetrahydrofuran / 1 h / 0 - 20 °C

2.2: CH₂Cl₂; tetrahydrofuran / 3 h / -78 °C

3.1: 92 percent / P₂O₅ / CHCl₃ / 3 h / 20 °C

4.1: 89 percent / Bu₃SnH; Et₃B / toluene; hexane / 2 h / -78 °C

5.1: 89 percent / TiCl₄ / CH₂Cl₂ / 0.5 h / 20 °C

6.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

With 2,6-dimethylpyridine; borane-THF; oxalyl dichloride; triethyl borane; tri-n-butyl-tin hydride; phosphorus pentoxide; titanium tetrachloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; chloroform; toluene; 1.1: Swern oxidation;
DOI:10.1021/jo034901c

Reference yield:

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

: 625109-64-0
ethyl (2R,3R,4S)-3-(tert-butyldimethylsiloxy)-5-(tert-butyldiphenylsiloxy)-2,4-dimethylpentanoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: BH₃*THF / CH₂Cl₂; tetrahydrofuran / 1 h / 0 - 20 °C

1.2: CH₂Cl₂; tetrahydrofuran / 3 h / -78 °C

2.1: 92 percent / P₂O₅ / CHCl₃ / 3 h / 20 °C

3.1: 89 percent / Bu₃SnH; Et₃B / toluene; hexane / 2 h / -78 °C

4.1: 89 percent / TiCl₄ / CH₂Cl₂ / 0.5 h / 20 °C

5.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

With 2,6-dimethylpyridine; borane-THF; triethyl borane; tri-n-butyl-tin hydride; phosphorus pentoxide; titanium tetrachloride; In tetrahydrofuran; hexane; dichloromethane; chloroform; toluene;
DOI:10.1021/jo034901c