ethyl (3R)-(tert-butyldimethylsilyloxy)-5-oxo-6-(triphenylphosphoranylidene)-hexanoate

Base Information

Chemical Name:ethyl (3R)-(tert-butyldimethylsilyloxy)-5-oxo-6-(triphenylphosphoranylidene)-hexanoate
CAS No.:917752-46-6
Molecular Formula:C₃₂H₄₁O₄PSi
Molecular Weight:548.734
Hs Code.:

Synonyms:ethyl (3R)-(tert-butyldimethylsilyloxy)-5-oxo-6-(triphenylphosphoranylidene)-hexanoate

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Chemical Property of ethyl (3R)-(tert-butyldimethylsilyloxy)-5-oxo-6-(triphenylphosphoranylidene)-hexanoate

Chemical Property:

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Technology Process of ethyl (3R)-(tert-butyldimethylsilyloxy)-5-oxo-6-(triphenylphosphoranylidene)-hexanoate

There total 13 articles about ethyl (3R)-(tert-butyldimethylsilyloxy)-5-oxo-6-(triphenylphosphoranylidene)-hexanoate 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:

: 1337981-93-7
C₁₄H₂₇BrO₄Si

: 603-35-0
triphenylphosphine

: 917752-46-6
ethyl (3R)-(tert-butyldimethylsilyloxy)-5-oxo-6-(triphenylphosphoranylidene)-hexanoate

Guidance literature:: With potassium carbonate; In chloroform; at -10 - 10 ℃; Product distribution / selectivity;

Reference yield:

: methyl (3S)-5-ethoxy-3-(tert-butyldimethylsilyl-oxy)-5-oxo-pentanoylcarbonate

: 1779-49-3
Methyltriphenylphosphonium bromide

: 917752-46-6
ethyl (3R)-(tert-butyldimethylsilyloxy)-5-oxo-6-(triphenylphosphoranylidene)-hexanoate

Guidance literature:: Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 1h;

methyl (3S)-5-ethoxy-3-(tert-butyldimethylsilyl-oxy)-5-oxo-pentanoylcarbonate; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 3h;
DOI:10.1021/acs.oprd.5b00057

Reference yield:

: 430434-51-8
(R)-ethyl 3-(tert-butyldimethylsilyloxy)hex-5-enoate

: 917752-46-6
ethyl (3R)-(tert-butyldimethylsilyloxy)-5-oxo-6-(triphenylphosphoranylidene)-hexanoate

Guidance literature:: Multi-step reaction with 3 steps

1: N-Bromosuccinimide / acetone / 0 - 35 °C

2: sodium hydrogencarbonate; sodium hypochlorite; tetrabutylammomium bromide; potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / N,N-dimethyl-formamide / -10 - 20 °C

3: potassium carbonate / chloroform / -10 - 10 °C

With sodium hypochlorite; N-Bromosuccinimide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutylammomium bromide; sodium hydrogencarbonate; potassium carbonate; potassium bromide; In chloroform; N,N-dimethyl-formamide; acetone; 3: Wittig Reaction;