methyl N^α-benzoyl-N^ε-(2''-trimethylsilyl)ethanesulfonyl-N^ε-4'''-methoxybenzyl-L-α-(2'Z-fluoro)vinyllysinate

Base Information

• Chemical Name: methyl N^α-benzoyl-N^ε-(2''-trimethylsilyl)ethanesulfonyl-N^ε-4'''-methoxybenzyl-L-α-(2'Z-fluoro)vinyllysinate
• CAS No.: 925451-54-3
• Molecular Formula: C₂₉H₄₁FN₂O₆SSi
• Molecular Weight: 592.804

Synonyms:methyl N^α-benzoyl-N^ε-(2''-trimethylsilyl)ethanesulfonyl-N^ε-4'''-methoxybenzyl-L-α-(2'Z-fluoro)vinyllysinate

Chemical Property of methyl N^α-benzoyl-N^ε-(2''-trimethylsilyl)ethanesulfonyl-N^ε-4'''-methoxybenzyl-L-α-(2'Z-fluoro)vinyllysinate

Chemical Property:

Purity/Quality:

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Technology Process of methyl N^α-benzoyl-N^ε-(2''-trimethylsilyl)ethanesulfonyl-N^ε-4'''-methoxybenzyl-L-α-(2'Z-fluoro)vinyllysinate

There total 13 articles about methyl N^α-benzoyl-N^ε-(2''-trimethylsilyl)ethanesulfonyl-N^ε-4'''-methoxybenzyl-L-α-(2'Z-fluoro)vinyllysinate 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:

methyl Nα-benzoyl-Nε-(2''-trimethylsilyl)ethanesulfonyl-Nε-4'''-methoxybenzyl-L-α-(2'E-benzenesulfonyl-2'-fluoro)vinyllysinate (925451-52-1) → methyl Nα-benzoyl-Nε-(2''-trimethylsilyl)ethanesulfonyl-Nε-4'''-methoxybenzyl-L-α-(2'Z-fluoro)vinyllysinate (925451-54-3)

Guidance literature:

methyl N^α-benzoyl-N^ε-(2''-trimethylsilyl)ethanesulfonyl-N^ε-4'''-methoxybenzyl-L-α-(2'E-benzenesulfonyl-2'-fluoro)vinyllysinate; With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 21h; Heating;

With methanol; acetyl chloride; at 0 ℃; for 2h;

DOI:10.1021/ja067240k

Reference yield:

N-(2'-trimethylsilyl)ethanesulfonyl-4-methoxybenzylamine (925451-33-8) → methyl Nα-benzoyl-Nε-(2''-trimethylsilyl)ethanesulfonyl-Nε-4'''-methoxybenzyl-L-α-(2'Z-fluoro)vinyllysinate (925451-54-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C

1.2: 77 percent / tetrahydrofuran; hexane / -78 - 20 °C

2.1: 91 percent / sodium iodide / acetone / 14 h / 50 °C / Heating

3.1: LDA; n-BuLi / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / -78 °C

3.2: tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 5 h / -78 °C

4.1: 96 percent / LiAlH₄ / tetrahydrofuran / 3 h / 0 °C

5.1: CrO₃; aq. H₂SO₄ / acetone / 0 - 20 °C

6.1: 1.21 g / diethyl ether

7.1: O₃ / CH₂Cl₂ / -78 °C

7.2: 75 percent / dimethyl sulfide / CH₂Cl₂ / 2 h / 20 °C

8.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

8.2: 79 percent / tetrahydrofuran / 3.5 h / 0 °C

9.1: AIBN; n-Bu₃SnH / benzene / 21 h / Heating

9.2: 0.44 g / acetyl chloride; methanol / 2 h / 0 °C

With chromium(VI) oxide; lithium aluminium tetrahydride; n-butyllithium; 2,2'-azobis(isobutyronitrile); sulfuric acid; tri-n-butyl-tin hydride; ozone; sodium iodide; lithium hexamethyldisilazane; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; acetone; benzene; 5.1: Jones oxidation;

DOI:10.1021/ja067240k

Reference yield:

N-(2'-trimethylsilyl)ethanesulfonyl-N-4''-iodobutyl-4-methoxybenzylamine (925451-38-3) → methyl Nα-benzoyl-Nε-(2''-trimethylsilyl)ethanesulfonyl-Nε-4'''-methoxybenzyl-L-α-(2'Z-fluoro)vinyllysinate (925451-54-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: LDA; n-BuLi / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / -78 °C

1.2: tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 5 h / -78 °C

2.1: 96 percent / LiAlH₄ / tetrahydrofuran / 3 h / 0 °C

3.1: CrO₃; aq. H₂SO₄ / acetone / 0 - 20 °C

4.1: 1.21 g / diethyl ether

5.1: O₃ / CH₂Cl₂ / -78 °C

5.2: 75 percent / dimethyl sulfide / CH₂Cl₂ / 2 h / 20 °C

6.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

6.2: 79 percent / tetrahydrofuran / 3.5 h / 0 °C

7.1: AIBN; n-Bu₃SnH / benzene / 21 h / Heating

7.2: 0.44 g / acetyl chloride; methanol / 2 h / 0 °C

With chromium(VI) oxide; lithium aluminium tetrahydride; n-butyllithium; 2,2'-azobis(isobutyronitrile); sulfuric acid; tri-n-butyl-tin hydride; ozone; lithium hexamethyldisilazane; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; acetone; benzene; 3.1: Jones oxidation;

DOI:10.1021/ja067240k

upstream raw materials:

methyl N^α-benzoyl-N^ε-(2''-trimethylsilyl)ethanesulfonyl-N^ε-4'''-methoxybenzyl-L-α-(2'E-benzenesulfonyl-2'-fluoro)vinyllysinate

N-(2'-trimethylsilyl)ethanesulfonyl-4-methoxybenzylamine

N-(2'-trimethylsilyl)ethanesulfonyl-N-(4''-chlorobutyl)-4-methoxybenzylamine

N-(2'-trimethylsilyl)ethanesulfonyl-N-4''-iodobutyl-4-methoxybenzylamine

Downstream raw materials:

methyl N^α-benzoyl-N^ε-(2''-trimethylsilyl)ethanesulfonyl-L-α-(2'Z-fluorovinyl)lysinate

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