methyl (2S,3R,R_S)-2-phenyl-3-(N-tert-butylsulfinamido)-16-(pyridin-3′-yl)hexadecanoate

Base Information

• Chemical Name: methyl (2S,3R,R_S)-2-phenyl-3-(N-tert-butylsulfinamido)-16-(pyridin-3′-yl)hexadecanoate
• CAS No.: 1569300-02-2
• Molecular Formula: C₃₂H₅₀N₂O₃S
• Molecular Weight: 542.827

Synonyms:methyl (2S,3R,R_S)-2-phenyl-3-(N-tert-butylsulfinamido)-16-(pyridin-3′-yl)hexadecanoate

Chemical Property of methyl (2S,3R,R_S)-2-phenyl-3-(N-tert-butylsulfinamido)-16-(pyridin-3′-yl)hexadecanoate

Chemical Property:

Purity/Quality:

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Technology Process of methyl (2S,3R,R_S)-2-phenyl-3-(N-tert-butylsulfinamido)-16-(pyridin-3′-yl)hexadecanoate

There total 5 articles about methyl (2S,3R,R_S)-2-phenyl-3-(N-tert-butylsulfinamido)-16-(pyridin-3′-yl)hexadecanoate 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: 99.0%

methyl (2S,3R,RS,Z)-2-phenyl-3-(N-tert-butylsulfinamido)-16-(pyridin-3′-yl)hexadec-13-enoate (1569300-00-0) → methyl (2S,3R,RS)-2-phenyl-3-(N-tert-butylsulfinamido)-16-(pyridin-3′-yl)hexadecanoate (1569300-02-2)

Guidance literature:

With palladium hydroxide, 20 wt% on carbon; hydrogen; In methanol; at 20 ℃; for 24h; under 760.051 Torr;

DOI:10.1021/ol500096r

Reference yield:

methyl (3R,RS)-2-phenyl-3-(N-tert-butylsulfinamido)-16-(pyridin-3′-yl)hexadec-13-enoate → methyl (2S,3R,RS)-2-phenyl-3-(N-tert-butylsulfinamido)-16-(pyridin-3′-yl)hexadecanoate (1569300-02-2)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium / methanol / 8 h / 0 °C

2: palladium hydroxide, 20 wt% on carbon; hydrogen / methanol / 24 h / 20 °C / 760.05 Torr

With palladium hydroxide, 20 wt% on carbon; hydrogen; sodium; In methanol;

DOI:10.1021/ol500096r

Reference yield:

(Z)-14-(pyridin-3'-yl)tetradec-11-en-1-ol (133835-21-9) → methyl (2S,3R,RS)-2-phenyl-3-(N-tert-butylsulfinamido)-16-(pyridin-3′-yl)hexadecanoate (1569300-02-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 3 h / 80 °C

2.1: pyridinium p-toluenesulfonate; magnesium sulfate / dichloromethane / 16 h / 20 °C

3.1: methylmagnesium bromide; magnesium bromide / diethyl ether; tetrahydrofuran / 1 h / -78 °C

3.2: 6 h / -78 °C

4.1: palladium hydroxide, 20 wt% on carbon; hydrogen / methanol / 24 h / 20 °C / 760.05 Torr

With palladium hydroxide, 20 wt% on carbon; methylmagnesium bromide; hydrogen; pyridinium p-toluenesulfonate; magnesium sulfate; magnesium bromide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate;

DOI:10.1021/ol500096r

upstream raw materials:

(Z)-14-(pyridin-3'-yl)tetradec-11-en-1-ol

(Z)-14-(pyridin-3′-yl)tetradec-11-enal

(E,R_S)-N-[(11Z)-(14-(pyridin-3′-yl))tetradec-11-en-1-ylidene]-tert-butylsulfinamide

methyl (2S,3R,R_S,Z)-2-phenyl-3-(N-tert-butylsulfinamido)-16-(pyridin-3′-yl)hexadec-13-enoate

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