(R_S,5S)-(-)-methyl 3-oxo-5-(p-toluenesulfinylamino)tetradeca-6,8-dienoate

Base Information

• Chemical Name: (R_S,5S)-(-)-methyl 3-oxo-5-(p-toluenesulfinylamino)tetradeca-6,8-dienoate
• CAS No.: 720682-29-1
• Molecular Formula: C₂₂H₃₁NO₄S
• Molecular Weight: 405.558

Synonyms:(R_S,5S)-(-)-methyl 3-oxo-5-(p-toluenesulfinylamino)tetradeca-6,8-dienoate

Chemical Property of (R_S,5S)-(-)-methyl 3-oxo-5-(p-toluenesulfinylamino)tetradeca-6,8-dienoate

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (R_S,5S)-(-)-methyl 3-oxo-5-(p-toluenesulfinylamino)tetradeca-6,8-dienoate

There total 4 articles about (R_S,5S)-(-)-methyl 3-oxo-5-(p-toluenesulfinylamino)tetradeca-6,8-dienoate 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: 78.0%

acetic acid methyl ester (79-20-9) + (RS,3S)-(-)-methyl 3-[N-(p-toluenesulfinyl)amino]dodeca-4,6-dienoate (720682-28-0) → (RS,5S)-(-)-methyl 3-oxo-5-(p-toluenesulfinylamino)tetradeca-6,8-dienoate (720682-29-1)

Guidance literature:

acetic acid methyl ester; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h;

(R_S,3S)-(-)-methyl 3-[N-(p-toluenesulfinyl)amino]dodeca-4,6-dienoate; In tetrahydrofuran; at -78 - -15 ℃; for 2.83333h; Further stages.;

DOI:10.1016/j.tet.2004.03.094

Reference yield:

trans,trans-2,4-decadienal (25152-84-5,65909-91-3) → (RS,5S)-(-)-methyl 3-oxo-5-(p-toluenesulfinylamino)tetradeca-6,8-dienoate (720682-29-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 75 percent / titanium(IV) ethoxide / CH₂Cl₂ / 12 h / 20 °C

2.1: NaHMDS / diethyl ether; tetrahydrofuran / 0.83 h / -78 °C

2.2: 77 percent / diethyl ether; tetrahydrofuran / 4 h / -78 °C

3.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

3.2: 78 percent / tetrahydrofuran / 2.83 h / -78 - -15 °C

With titanium(IV) tetraethanolate; sodium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1016/j.tet.2004.03.094

Reference yield:

(R)-p-toluenesulfinamide (247089-85-6) → (RS,5S)-(-)-methyl 3-oxo-5-(p-toluenesulfinylamino)tetradeca-6,8-dienoate (720682-29-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 75 percent / titanium(IV) ethoxide / CH₂Cl₂ / 12 h / 20 °C

2.1: NaHMDS / diethyl ether; tetrahydrofuran / 0.83 h / -78 °C

2.2: 77 percent / diethyl ether; tetrahydrofuran / 4 h / -78 °C

3.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

3.2: 78 percent / tetrahydrofuran / 2.83 h / -78 - -15 °C

With titanium(IV) tetraethanolate; sodium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1016/j.tet.2004.03.094

upstream raw materials:

acetic acid methyl ester

(R_S,3S)-(-)-methyl 3-[N-(p-toluenesulfinyl)amino]dodeca-4,6-dienoate

trans,trans-2,4-decadienal

(R)-p-toluenesulfinamide

Downstream raw materials:

(+)-preussin

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