ethyl (3R,5S)-6-(tert-butyldiphenylsiloxy)-3-hydroxy-5-(p-methoxybenzyloxy)hexanoate

Base Information

Chemical Name:ethyl (3R,5S)-6-(tert-butyldiphenylsiloxy)-3-hydroxy-5-(p-methoxybenzyloxy)hexanoate
CAS No.:950513-94-7
Molecular Formula:C₃₂H₄₂O₆Si
Molecular Weight:550.767
Hs Code.:

Synonyms:ethyl (3R,5S)-6-(tert-butyldiphenylsiloxy)-3-hydroxy-5-(p-methoxybenzyloxy)hexanoate

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Chemical Property of ethyl (3R,5S)-6-(tert-butyldiphenylsiloxy)-3-hydroxy-5-(p-methoxybenzyloxy)hexanoate

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Technology Process of ethyl (3R,5S)-6-(tert-butyldiphenylsiloxy)-3-hydroxy-5-(p-methoxybenzyloxy)hexanoate

There total 5 articles about ethyl (3R,5S)-6-(tert-butyldiphenylsiloxy)-3-hydroxy-5-(p-methoxybenzyloxy)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:

: 950513-92-5
(3R,5S)-6-(tert-butyldiphenylsiloxy)-3-hydroxy-1-[(4'R)-4'-isopropyl-2'-thioxothiazolidin-3'-yl]-5-(4-methoxybenzyloxy)-hexan-1-one

: 64-17-5
ethanol

: 950513-94-7
ethyl (3R,5S)-6-(tert-butyldiphenylsiloxy)-3-hydroxy-5-(p-methoxybenzyloxy)hexanoate

: 110199-16-1
4(R)-isopropyl-1,3-thiazolidine-2-thione

Guidance literature:: With dmap; at 20 ℃; for 18h;
DOI:10.1016/j.tet.2007.05.093

Reference yield:

: 124655-05-6
(S)-methyl 4-(tert-butyldiphenylsilyloxy)-3-hydroxybutanoate

: 950513-94-7
ethyl (3R,5S)-6-(tert-butyldiphenylsiloxy)-3-hydroxy-5-(p-methoxybenzyloxy)hexanoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 77 percent / LiAlH₄ / tetrahydrofuran / 1.25 h / 0 °C

2.1: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.83 h / 20 °C

3.1: N-ethylpiperidine / tin(II) triflate / CH₂Cl₂ / 4 h / -50 °C

3.2: 76 percent / CH₂Cl₂ / 7 h / -78 °C

4.1: 1.99 g / DMAP / 18 h / 20 °C

With 1-ethyl-piperidine; dmap; lithium aluminium tetrahydride; Dess-Martin periodane; tin(II) trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tet.2007.05.093

Reference yield:

: 221677-48-1
(3S)-4-[1-(tert-butyl)-1,1-diphenylsilyl]oxy-3-[(4-methoxybenzyl)oxy]butan-1-ol

: 950513-94-7
ethyl (3R,5S)-6-(tert-butyldiphenylsiloxy)-3-hydroxy-5-(p-methoxybenzyloxy)hexanoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.83 h / 20 °C

2.1: N-ethylpiperidine / tin(II) triflate / CH₂Cl₂ / 4 h / -50 °C

2.2: 76 percent / CH₂Cl₂ / 7 h / -78 °C

3.1: 1.99 g / DMAP / 18 h / 20 °C

With 1-ethyl-piperidine; dmap; Dess-Martin periodane; tin(II) trifluoromethanesulfonate; In dichloromethane;
DOI:10.1016/j.tet.2007.05.093