(E)-5-(2-tert-butyldimethylsilyloxy-5-methoxyphenyl)pent-2-enyl methyl carbonate

Base Information

Chemical Name:(E)-5-(2-tert-butyldimethylsilyloxy-5-methoxyphenyl)pent-2-enyl methyl carbonate
CAS No.:783333-01-7
Molecular Formula:C₂₀H₃₂O₅Si
Molecular Weight:380.557
Hs Code.:

Synonyms:(E)-5-(2-tert-butyldimethylsilyloxy-5-methoxyphenyl)pent-2-enyl methyl carbonate

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Chemical Property of (E)-5-(2-tert-butyldimethylsilyloxy-5-methoxyphenyl)pent-2-enyl methyl carbonate

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Technology Process of (E)-5-(2-tert-butyldimethylsilyloxy-5-methoxyphenyl)pent-2-enyl methyl carbonate

There total 4 articles about (E)-5-(2-tert-butyldimethylsilyloxy-5-methoxyphenyl)pent-2-enyl methyl carbonate 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%

: 79-22-1
methyl chloroformate

: 783333-02-8
(E)-5-(2-((tert-butyldimethylsilyl)oxy)-5-methoxyphenyl)pent-2-en-1-ol

: 783333-01-7
(E)-5-(2-tert-butyldimethylsilyloxy-5-methoxyphenyl)pent-2-enyl methyl carbonate

Guidance literature:: With pyridine; dmap; In dichloromethane; at 20 ℃; for 24h;
DOI:10.1021/ja048078t

Reference yield:

: 736985-50-5
2-allyl-1-(tert-butyldimethylsilyloxy)-4-methoxybenzene

: 783333-01-7
(E)-5-(2-tert-butyldimethylsilyloxy-5-methoxyphenyl)pent-2-enyl methyl carbonate

Guidance literature:: Multi-step reaction with 5 steps

1.1: BH₃*THF / tetrahydrofuran / 1.5 h / 20 °C

1.2: 72 percent / aq. NaOH; aq. H₂O₂ / 2 h / 0 °C

2.1: 98 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: 94 percent / benzene / 20 °C

4.1: 76 percent / DIBAL / tetrahydrofuran; toluene / -78 - 20 °C

5.1: 91 percent / DMAP; pyridine / CH₂Cl₂ / 24 h / 20 °C

With pyridine; dmap; borane-THF; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; toluene; benzene; 2.1: Swern oxidation / 3.1: Wittig reaction;
DOI:10.1021/ja048078t

Reference yield:

: 736985-53-8
3-[(2-tert-butyldimethylsilanyloxy)-5-methoxyphenyl]-propionaldehyde

: 783333-01-7
(E)-5-(2-tert-butyldimethylsilyloxy-5-methoxyphenyl)pent-2-enyl methyl carbonate

Guidance literature:: Multi-step reaction with 3 steps

1: 94 percent / benzene / 20 °C

2: 76 percent / DIBAL / tetrahydrofuran; toluene / -78 - 20 °C

3: 91 percent / DMAP; pyridine / CH₂Cl₂ / 24 h / 20 °C

With pyridine; dmap; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; toluene; benzene; 1: Wittig reaction;
DOI:10.1021/ja048078t