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

Base Information

• Chemical Name: methyl (2R,3R,R_S,E)-2-phenyl-3-(N-tert-butylsulfinamido)-16-(pyridin-3′-yl)hexadec-13-enoate
• CAS No.: 1569300-08-8
• Molecular Formula: C₃₂H₄₈N₂O₃S
• Molecular Weight: 540.811

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

Chemical Property of methyl (2R,3R,R_S,E)-2-phenyl-3-(N-tert-butylsulfinamido)-16-(pyridin-3′-yl)hexadec-13-enoate

Chemical Property:

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Technology Process of methyl (2R,3R,R_S,E)-2-phenyl-3-(N-tert-butylsulfinamido)-16-(pyridin-3′-yl)hexadec-13-enoate

There total 4 articles about methyl (2R,3R,R_S,E)-2-phenyl-3-(N-tert-butylsulfinamido)-16-(pyridin-3′-yl)hexadec-13-enoate 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: 60.0%

(E,RS)-N-[(11Z)-(14-(pyridin-3′-yl))tetradec-11-en-1-ylidene]-tert-butylsulfinamide (1569299-99-5) + benzeneacetic acid methyl ester (101-41-7) → methyl (2R,3R,RS,E)-2-phenyl-3-(N-tert-butylsulfinamido)-16-(pyridin-3′-yl)hexadec-13-enoate (1569300-08-8) + methyl (2S,3R,RS,Z)-2-phenyl-3-(N-tert-butylsulfinamido)-16-(pyridin-3′-yl)hexadec-13-enoate (1569300-00-0) + methyl (2R,3R,RS,Z)-2-phenyl-3-(N-tert-butylsulfinamido)-16-(pyridin-3′-yl)hexadec-13-enoate (1569300-01-1)

Guidance literature:

benzeneacetic acid methyl ester; With methylmagnesium bromide; magnesium bromide; In tetrahydrofuran; diethyl ether; at -78 ℃; for 1h;

(E,R_S)-N-[(11Z)-(14-(pyridin-3′-yl))tetradec-11-en-1-ylidene]-tert-butylsulfinamide; In tetrahydrofuran; diethyl ether; at -78 ℃; for 6h; Reagent/catalyst;

DOI:10.1021/ol500096r

Reference yield: 9.0%

methyl (3R,RS)-2-phenyl-3-(N-tert-butylsulfinamido)-16-(pyridin-3′-yl)hexadec-13-enoate → methyl (2R,3R,RS,E)-2-phenyl-3-(N-tert-butylsulfinamido)-16-(pyridin-3′-yl)hexadec-13-enoate (1569300-08-8) + methyl (2S,3R,RS,Z)-2-phenyl-3-(N-tert-butylsulfinamido)-16-(pyridin-3′-yl)hexadec-13-enoate (1569300-00-0) + methyl (2R,3R,RS,Z)-2-phenyl-3-(N-tert-butylsulfinamido)-16-(pyridin-3′-yl)hexadec-13-enoate (1569300-01-1)

Guidance literature:

With sodium; In methanol; at 0 ℃; for 8h;

DOI:10.1021/ol500096r

Reference yield:

(Z)-14-(pyridin-3'-yl)tetradec-11-en-1-ol (133835-21-9) → methyl (2R,3R,RS,E)-2-phenyl-3-(N-tert-butylsulfinamido)-16-(pyridin-3′-yl)hexadec-13-enoate (1569300-08-8)

Guidance literature:

Multi-step reaction with 3 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

With methylmagnesium bromide; pyridinium p-toluenesulfonate; magnesium sulfate; magnesium bromide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate;

DOI:10.1021/ol500096r

upstream raw materials:

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

benzeneacetic acid methyl ester

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

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

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