methyl N-acetyl-5-(2-methoxy-5-methylphenyl)-1-[2-(trimethylsilyl)ethoxymethyl]-L-histidinate

Base Information

Chemical Name:methyl N-acetyl-5-(2-methoxy-5-methylphenyl)-1-[2-(trimethylsilyl)ethoxymethyl]-L-histidinate
CAS No.:955134-24-4
Molecular Formula:C₂₃H₃₅N₃O₅Si
Molecular Weight:461.634
Hs Code.:

Synonyms:methyl N-acetyl-5-(2-methoxy-5-methylphenyl)-1-[2-(trimethylsilyl)ethoxymethyl]-L-histidinate

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Chemical Property of methyl N-acetyl-5-(2-methoxy-5-methylphenyl)-1-[2-(trimethylsilyl)ethoxymethyl]-L-histidinate

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Technology Process of methyl N-acetyl-5-(2-methoxy-5-methylphenyl)-1-[2-(trimethylsilyl)ethoxymethyl]-L-histidinate

There total 4 articles about methyl N-acetyl-5-(2-methoxy-5-methylphenyl)-1-[2-(trimethylsilyl)ethoxymethyl]-L-histidinate 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: 36.0%

: 955134-22-2
methyl N-acetyl-5-bromo-1-[2-(trimethylsilyl)ethoxymethyl]-L-histidinate

: 127972-00-3
2-methoxy-5-methylphenyl boronic acid

: 955134-24-4
methyl N-acetyl-5-(2-methoxy-5-methylphenyl)-1-[2-(trimethylsilyl)ethoxymethyl]-L-histidinate

Guidance literature:: With potassium fluoride; tris-(o-tolyl)phosphine; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In methanol; water; toluene; at 110 ℃; for 1h; microwave irradiation;
DOI:10.1016/j.tet.2007.08.010

Reference yield:

: 955134-08-4
methyl N-acetyl-5-bromo-L-histidinate

: 955134-24-4
methyl N-acetyl-5-(2-methoxy-5-methylphenyl)-1-[2-(trimethylsilyl)ethoxymethyl]-L-histidinate

Guidance literature:: Multi-step reaction with 2 steps

1: 49 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / dimethylformamide / 1.5 h / 0 °C

2: 36 percent / KF; P(o-tolyl)3 / Pd₂(dba)3 / toluene; H₂O; methanol / 1 h / 110 °C / microwave irradiation

With potassium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; tris-(o-tolyl)phosphine; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In methanol; water; N,N-dimethyl-formamide; toluene; 2: Suzuki coupling;
DOI:10.1016/j.tet.2007.08.010

Reference yield:

: 2497-02-1
N-acetyl-L-histidine

: 955134-24-4
methyl N-acetyl-5-(2-methoxy-5-methylphenyl)-1-[2-(trimethylsilyl)ethoxymethyl]-L-histidinate

Guidance literature:: Multi-step reaction with 4 steps

1: 90 percent / thionyl chloride / 2 h / 20 °C

2: 60 percent / N-bromosuccinimide / acetonitrile / 0.25 h / 0 °C

3: 49 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / dimethylformamide / 1.5 h / 0 °C

4: 36 percent / KF; P(o-tolyl)3 / Pd₂(dba)3 / toluene; H₂O; methanol / 1 h / 110 °C / microwave irradiation

With potassium fluoride; N-Bromosuccinimide; thionyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; tris-(o-tolyl)phosphine; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In methanol; water; N,N-dimethyl-formamide; toluene; acetonitrile; 4: Suzuki coupling;
DOI:10.1016/j.tet.2007.08.010