(5R,7S)-tert-butyl 8-(tert-butyldiphenylsiloxy)-5-hydroxy-7-(4-methoxybenzyloxy)-3-oxooctanoate

Base Information

Chemical Name:(5R,7S)-tert-butyl 8-(tert-butyldiphenylsiloxy)-5-hydroxy-7-(4-methoxybenzyloxy)-3-oxooctanoate
CAS No.:950513-95-8
Molecular Formula:C₃₆H₄₈O₇Si
Molecular Weight:620.858
Hs Code.:

Synonyms:(5R,7S)-tert-butyl 8-(tert-butyldiphenylsiloxy)-5-hydroxy-7-(4-methoxybenzyloxy)-3-oxooctanoate

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Chemical Property of (5R,7S)-tert-butyl 8-(tert-butyldiphenylsiloxy)-5-hydroxy-7-(4-methoxybenzyloxy)-3-oxooctanoate

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Technology Process of (5R,7S)-tert-butyl 8-(tert-butyldiphenylsiloxy)-5-hydroxy-7-(4-methoxybenzyloxy)-3-oxooctanoate

There total 6 articles about (5R,7S)-tert-butyl 8-(tert-butyldiphenylsiloxy)-5-hydroxy-7-(4-methoxybenzyloxy)-3-oxooctanoate 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:

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

: 950513-95-8
(5R,7S)-tert-butyl 8-(tert-butyldiphenylsiloxy)-5-hydroxy-7-(4-methoxybenzyloxy)-3-oxooctanoate

Guidance literature:: Multi-step reaction with 6 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

5.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

5.2: tetrahydrofuran / 0.5 h / -78 °C

With 1-ethyl-piperidine; dmap; lithium aluminium tetrahydride; Dess-Martin periodane; lithium hexamethyldisilazane; 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

: 950513-95-8
(5R,7S)-tert-butyl 8-(tert-butyldiphenylsiloxy)-5-hydroxy-7-(4-methoxybenzyloxy)-3-oxooctanoate

Guidance literature:: Multi-step reaction with 4 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

4.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

4.2: tetrahydrofuran / 0.5 h / -78 °C

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

Reference yield:

: 478491-16-6
(3S)-4-(tert-butyldiphenylsilanyloxy)-(4-methoxybenzyloxy) butyraldehyde

: 950513-95-8
(5R,7S)-tert-butyl 8-(tert-butyldiphenylsiloxy)-5-hydroxy-7-(4-methoxybenzyloxy)-3-oxooctanoate

Guidance literature:: Multi-step reaction with 3 steps

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

1.2: 76 percent / CH₂Cl₂ / 7 h / -78 °C

2.1: 1.99 g / DMAP / 18 h / 20 °C

3.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

3.2: tetrahydrofuran / 0.5 h / -78 °C

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