(3R,4S,5S)-(E)-9-(tert-butyldiphenylsilyloxy)-4-(para-methoxybenzyloxy)-1-methoxy-3,5-dimethyl-non-1,6-diene

Base Information

Chemical Name:(3R,4S,5S)-(E)-9-(tert-butyldiphenylsilyloxy)-4-(para-methoxybenzyloxy)-1-methoxy-3,5-dimethyl-non-1,6-diene
CAS No.:313696-91-2
Molecular Formula:C₃₆H₄₈O₄Si
Molecular Weight:572.86
Hs Code.:

Synonyms:(3R,4S,5S)-(E)-9-(tert-butyldiphenylsilyloxy)-4-(para-methoxybenzyloxy)-1-methoxy-3,5-dimethyl-non-1,6-diene

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Chemical Property of (3R,4S,5S)-(E)-9-(tert-butyldiphenylsilyloxy)-4-(para-methoxybenzyloxy)-1-methoxy-3,5-dimethyl-non-1,6-diene

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Technology Process of (3R,4S,5S)-(E)-9-(tert-butyldiphenylsilyloxy)-4-(para-methoxybenzyloxy)-1-methoxy-3,5-dimethyl-non-1,6-diene

There total 7 articles about (3R,4S,5S)-(E)-9-(tert-butyldiphenylsilyloxy)-4-(para-methoxybenzyloxy)-1-methoxy-3,5-dimethyl-non-1,6-diene 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:

: 4009-98-7
(methoxymethyl)triphenylphosphonium chloride

: 313696-90-1
(2S,3S,4S)-(E)-8-(tert-butyldiphenylsilyloxy)-3-(para-methoxybenzyloxy)-2,4-dimethyl-5-octen-1-al

: 313696-91-2
(3R,4S,5S)-(E)-9-(tert-butyldiphenylsilyloxy)-4-(para-methoxybenzyloxy)-1-methoxy-3,5-dimethyl-non-1,6-diene

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -10 ℃; for 0.5h;
DOI:10.1021/ja002377a

Reference yield:

: 123-11-5
4-methoxy-benzaldehyde

: 313696-91-2
(3R,4S,5S)-(E)-9-(tert-butyldiphenylsilyloxy)-4-(para-methoxybenzyloxy)-1-methoxy-3,5-dimethyl-non-1,6-diene

Guidance literature:: Multi-step reaction with 4 steps

1: 89 percent / p-toluene sulfonic acid monohydrade / benzene / 20 h / 25 °C

2: 100 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 15 h / -50 °C

3: 98 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 3 h / 20 °C

4: LDA / tetrahydrofuran; hexane / 0.5 h / -10 °C

With pyridine; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; benzene;
DOI:10.1021/ja002377a

Reference yield:

: (4S)-(E)-6-(tert-butyldiphenylsilyloxy)-4-(dimethylphenyl)silyl-2-hexene

: 313696-91-2
(3R,4S,5S)-(E)-9-(tert-butyldiphenylsilyloxy)-4-(para-methoxybenzyloxy)-1-methoxy-3,5-dimethyl-non-1,6-diene

Guidance literature:: Multi-step reaction with 6 steps

1: TiCl₄ / CH₂Cl₂ / 5 h / -78 °C

2: 90 percent / boron trichloride / toluene; hexane / 5 h / -78 °C

3: 89 percent / p-toluene sulfonic acid monohydrade / benzene / 20 h / 25 °C

4: 100 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 15 h / -50 °C

5: 98 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 3 h / 20 °C

6: LDA / tetrahydrofuran; hexane / 0.5 h / -10 °C

With pyridine; boron trichloride; titanium tetrachloride; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; toluene; benzene;
DOI:10.1021/ja002377a