(3S)-3-((R)-2-(tert-butyldiphenylsilyloxy)-1-(triethylsilyloxy)ethyl)-2-methyl-4-pentenal

Base Information

Chemical Name:(3S)-3-((R)-2-(tert-butyldiphenylsilyloxy)-1-(triethylsilyloxy)ethyl)-2-methyl-4-pentenal
CAS No.:937068-01-4
Molecular Formula:C₃₀H₄₆O₃Si₂
Molecular Weight:510.864
Hs Code.:

Synonyms:(3S)-3-((R)-2-(tert-butyldiphenylsilyloxy)-1-(triethylsilyloxy)ethyl)-2-methyl-4-pentenal

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Chemical Property of (3S)-3-((R)-2-(tert-butyldiphenylsilyloxy)-1-(triethylsilyloxy)ethyl)-2-methyl-4-pentenal

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Technology Process of (3S)-3-((R)-2-(tert-butyldiphenylsilyloxy)-1-(triethylsilyloxy)ethyl)-2-methyl-4-pentenal

There total 6 articles about (3S)-3-((R)-2-(tert-butyldiphenylsilyloxy)-1-(triethylsilyloxy)ethyl)-2-methyl-4-pentenal 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: 86.0%

: 937067-99-7
(3S)-3-((R)-2-(tert-butyldiphenylsilyloxy)-1-(triethylsilyloxy)ethyl)-2-methyl-4-pentenenitrile

: 937068-01-4
(3S)-3-((R)-2-(tert-butyldiphenylsilyloxy)-1-(triethylsilyloxy)ethyl)-2-methyl-4-pentenal

Guidance literature:: With diisobutylaluminium hydride; In toluene; at -78 - -5 ℃; for 2.5h;
DOI:10.1021/jo0626461

Reference yield:

: 937067-97-5
(3S)-3-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-2-methyl-4-pentenenitrile

: 937068-01-4
(3S)-3-((R)-2-(tert-butyldiphenylsilyloxy)-1-(triethylsilyloxy)ethyl)-2-methyl-4-pentenal

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / pyridine; DMAP / 20 h / 20 °C

2: 86 percent / Dibal / toluene / 2.5 h / -78 - -5 °C

With pyridine; dmap; diisobutylaluminium hydride; In toluene;
DOI:10.1021/jo0626461

Reference yield:

: 92808-78-1
(E)-4-(tert-butyldiphenylsilyloxy)-2-buten-1-ol

: 937068-01-4
(3S)-3-((R)-2-(tert-butyldiphenylsilyloxy)-1-(triethylsilyloxy)ethyl)-2-methyl-4-pentenal

Guidance literature:: Multi-step reaction with 6 steps

1.1: (+)-diethyl L-tartrate; titanium(IV) isopropoxide / CH₂Cl₂ / 0.33 h / -30 - -20 °C

1.2: tert-butyl hydroperoxide / CH₂Cl₂ / 5.5 h / -30 - -20 °C

2.1: Dess-Martin reagent / CH₂Cl₂ / 2.5 h / 20 °C

3.1: KOtBu / tetrahydrofuran / 0.5 h / 0 °C

3.2: 14.0 g / tetrahydrofuran / 2 h / 20 °C

4.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C

4.2: 52 percent / tetrahydrofuran / 2 h / -78 - -10 °C

5.1: 95 percent / pyridine; DMAP / 20 h / 20 °C

6.1: 86 percent / Dibal / toluene / 2.5 h / -78 - -5 °C

With pyridine; titanium(IV) isopropylate; dmap; n-butyllithium; diethyl (2R,3R)-tartrate; potassium tert-butylate; diisobutylaluminium hydride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/jo0626461