methyl (2E,4S)-4-(tert-butyldimethylsilyloxy)-5-[3-(methoxymethyl)phenyl]-2-pentenoate

Base Information

Chemical Name:methyl (2E,4S)-4-(tert-butyldimethylsilyloxy)-5-[3-(methoxymethyl)phenyl]-2-pentenoate
CAS No.:1369917-42-9
Molecular Formula:C₂₀H₃₂O₄Si
Molecular Weight:364.557
Hs Code.:

Synonyms:methyl (2E,4S)-4-(tert-butyldimethylsilyloxy)-5-[3-(methoxymethyl)phenyl]-2-pentenoate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of methyl (2E,4S)-4-(tert-butyldimethylsilyloxy)-5-[3-(methoxymethyl)phenyl]-2-pentenoate

Chemical Property:

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Technology Process of methyl (2E,4S)-4-(tert-butyldimethylsilyloxy)-5-[3-(methoxymethyl)phenyl]-2-pentenoate

There total 1 articles about methyl (2E,4S)-4-(tert-butyldimethylsilyloxy)-5-[3-(methoxymethyl)phenyl]-2-pentenoate 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: 91.0%

: 67-56-1
methanol

: 201230-82-2
carbon monoxide

: 253350-40-2
3-(S)-tert-butyldimethylsilyloxy-1-iodo-4-(3-methoxymethyl)phenyl-1-butene

: 1369917-42-9
methyl (2E,4S)-4-(tert-butyldimethylsilyloxy)-5-[3-(methoxymethyl)phenyl]-2-pentenoate

Guidance literature:: With bis-triphenylphosphine-palladium(II) chloride; triethylamine; In acetonitrile; at 55 ℃; for 12h; Inert atmosphere;
DOI:10.1248/cpb.59.1494

Reference yield:

: 1369917-42-9
methyl (2E,4S)-4-(tert-butyldimethylsilyloxy)-5-[3-(methoxymethyl)phenyl]-2-pentenoate

: 1369917-43-0
(2E,4S)-4-(tert-butyldimethylsilyloxy)-5-[3-(methoxymethyl)phenyl]-2-penten-1-ol

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; toluene; at -70 - -20 ℃; for 1h; Inert atmosphere;
DOI:10.1248/cpb.59.1494

Reference yield:

: 1369917-42-9
methyl (2E,4S)-4-(tert-butyldimethylsilyloxy)-5-[3-(methoxymethyl)phenyl]-2-pentenoate

: 1369917-02-1
7-[{(2E,4S)-4-hydroxy-5-[3-(methoxymethyl)phenyl]pent-2-enyl}-(methylsulfonyl)amino]heptanoic acid

Guidance literature:: Multi-step reaction with 5 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -70 - -20 °C / Inert atmosphere

2.1: triethylamine / tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere

3.2: 0.42 h / 0 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

5.1: water; sodium hydroxide / methanol / 1.5 h / 20 °C

5.2: Cooling with ice

With tetrabutyl ammonium fluoride; water; sodium hydride; diisobutylaluminium hydride; triethylamine; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil;
DOI:10.1248/cpb.59.1494