(2S,3R,4S)-1-(tert-butyldiphenylsilyl)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylpentan-1-one

Base Information

Chemical Name:(2S,3R,4S)-1-(tert-butyldiphenylsilyl)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylpentan-1-one
CAS No.:1428137-60-3
Molecular Formula:C₃₁H₄₀O₄Si
Molecular Weight:504.742
Hs Code.:

Synonyms:(2S,3R,4S)-1-(tert-butyldiphenylsilyl)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylpentan-1-one

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Chemical Property of (2S,3R,4S)-1-(tert-butyldiphenylsilyl)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylpentan-1-one

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Technology Process of (2S,3R,4S)-1-(tert-butyldiphenylsilyl)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylpentan-1-one

There total 2 articles about (2S,3R,4S)-1-(tert-butyldiphenylsilyl)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylpentan-1-one 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: 62.0%

: 1428137-64-7
1-(tert-butyldiphenylsilyl)prop-2-en-1-ol

: 132969-60-9
(2S)-3-[(4-methoxybenzyl)oxy]-2-methylpropanal

: (anti,E)-1-(tert-butyldiphenylsilyl)-3-hydroxy-2-methyl-5-phenylpent-4-en-1-one

: 1428137-56-7
(2R,3S,4S)-1-(tert-butyldiphenylsilyl)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylpentan-1-one

: 1428137-60-3
(2S,3R,4S)-1-(tert-butyldiphenylsilyl)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylpentan-1-one

: 1428137-58-9
(2S,3S,4S)-1-(tert-butyldiphenylsilyl)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylpentan-1-one

Guidance literature:: With (2,2′-bis(biphenylphosphino)-1,1′-binaphthalene)NiCl2; lithium triethylborohydride; magnesium bromide; In tetrahydrofuran; at -40 ℃; for 24h; Overall yield = 92 %; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/ol4003064

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: (anti,E)-1-(tert-butyldiphenylsilyl)-3-hydroxy-2-methyl-5-phenylpent-4-en-1-one

: 1428137-60-3
(2S,3R,4S)-1-(tert-butyldiphenylsilyl)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylpentan-1-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: lithium / tetrahydrofuran / 48 h / 20 °C / Inert atmosphere

1.2: 0.5 h / -80 °C / Inert atmosphere

2.1: lithium triethylborohydride; (2,2′-bis(biphenylphosphino)-1,1′-binaphthalene)NiCl2; magnesium bromide / tetrahydrofuran / 24 h / -40 °C / Inert atmosphere

With (2,2′-bis(biphenylphosphino)-1,1′-binaphthalene)NiCl2; lithium; lithium triethylborohydride; magnesium bromide; In tetrahydrofuran;
DOI:10.1021/ol4003064