(2R,3S)-methyl 3-(3-bromo-4-methoxyphenyl)-3-((tert-butyldimethylsilyl)oxy)-2-(methylamino)propanoate

Base Information

• Chemical Name: (2R,3S)-methyl 3-(3-bromo-4-methoxyphenyl)-3-((tert-butyldimethylsilyl)oxy)-2-(methylamino)propanoate
• CAS No.: 1352147-54-6
• Molecular Formula: C₁₈H₃₀BrNO₄Si
• Molecular Weight: 432.43

Synonyms:(2R,3S)-methyl 3-(3-bromo-4-methoxyphenyl)-3-((tert-butyldimethylsilyl)oxy)-2-(methylamino)propanoate

Chemical Property of (2R,3S)-methyl 3-(3-bromo-4-methoxyphenyl)-3-((tert-butyldimethylsilyl)oxy)-2-(methylamino)propanoate

Chemical Property:

Purity/Quality:

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Technology Process of (2R,3S)-methyl 3-(3-bromo-4-methoxyphenyl)-3-((tert-butyldimethylsilyl)oxy)-2-(methylamino)propanoate

There total 6 articles about (2R,3S)-methyl 3-(3-bromo-4-methoxyphenyl)-3-((tert-butyldimethylsilyl)oxy)-2-(methylamino)propanoate 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: 73.0%

(2R,3S)-methyl 3-(3-bromo-4-methoxyphenyl)-3-((tert-butyldimethylsilyl)oxy)-2-(((1R,2S)-2-hydroxy 1,2diphenylethyl)(methyl)amino)propanoate (1352147-53-5) → (2R,3S)-methyl 3-(3-bromo-4-methoxyphenyl)-3-((tert-butyldimethylsilyl)oxy)-2-(methylamino)propanoate (1352147-54-6)

Guidance literature:

(2R,3S)-methyl 3-(3-bromo-4-methoxyphenyl)-3-((tert-butyldimethylsilyl)oxy)-2-(((1R,2S)-2-hydroxy 1,2diphenylethyl)(methyl)amino)propanoate; With lead(IV) tetraacetate; In dichloromethane; acetonitrile; at 0 ℃; for 0.5h; Inert atmosphere;

With water; sodium hydrogencarbonate; In dichloromethane; acetonitrile;

DOI:10.1016/j.tetlet.2011.11.069

Reference yield:

benzyl (2S,3R)-(+)-6-tert-butyldimethylsilyloxy-2,3-diphenyl-4-morpholin-5-enecarboxylate (911319-41-0) → (2R,3S)-methyl 3-(3-bromo-4-methoxyphenyl)-3-((tert-butyldimethylsilyl)oxy)-2-(methylamino)propanoate (1352147-54-6)

Guidance literature:

Multi-step reaction with 5 steps

1: copper(II) bis(trifluoromethanesulfonate) / dichloromethane / 2.5 h / 20 °C

2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 7 h / 760.05 Torr

3: zinc(II) chloride / tetrahydrofuran; diethyl ether / 24 h / 80 °C / Inert atmosphere

4: sodium cyanoborohydride; acetic acid / tetrahydrofuran; acetonitrile / 6 h

5: lead(IV) tetraacetate / dichloromethane; acetonitrile / 0.5 h / 0 °C / Inert atmosphere

With palladium 10% on activated carbon; hydrogen; lead(IV) tetraacetate; copper(II) bis(trifluoromethanesulfonate); sodium cyanoborohydride; acetic acid; zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; acetonitrile; 1: Mukaiyama aldol reaction;

DOI:10.1016/j.tetlet.2011.11.069

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (2R,3S)-methyl 3-(3-bromo-4-methoxyphenyl)-3-((tert-butyldimethylsilyl)oxy)-2-(methylamino)propanoate (1352147-54-6)

Guidance literature:

Multi-step reaction with 6 steps

1: sodium hexamethyldisilazane / tetrahydrofuran / -78 - 20 °C

2: copper(II) bis(trifluoromethanesulfonate) / dichloromethane / 2.5 h / 20 °C

3: palladium 10% on activated carbon; hydrogen / ethyl acetate / 7 h / 760.05 Torr

4: zinc(II) chloride / tetrahydrofuran; diethyl ether / 24 h / 80 °C / Inert atmosphere

5: sodium cyanoborohydride; acetic acid / tetrahydrofuran; acetonitrile / 6 h

6: lead(IV) tetraacetate / dichloromethane; acetonitrile / 0.5 h / 0 °C / Inert atmosphere

With palladium 10% on activated carbon; hydrogen; lead(IV) tetraacetate; sodium hexamethyldisilazane; copper(II) bis(trifluoromethanesulfonate); sodium cyanoborohydride; acetic acid; zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; acetonitrile; 2: Mukaiyama aldol reaction;

DOI:10.1016/j.tetlet.2011.11.069

upstream raw materials:

benzyl (2S,3R)-(+)-6-tert-butyldimethylsilyloxy-2,3-diphenyl-4-morpholin-5-enecarboxylate

(2R,3S)-methyl 3-(3-bromo-4-methoxyphenyl)-3-((tert-butyldimethylsilyl)oxy)-2-(((1R,2S)-2-hydroxy-1,2-diphenylethyl)amino)propanoate

(2R,3S)-methyl 3-(3-bromo-4-methoxyphenyl)-3-((tert-butyldimethylsilyl)oxy)-2-(((1R,2S)-2-hydroxy 1,2diphenylethyl)(methyl)amino)propanoate

(3R,5R,6S)-benzyl 3-((3-bromo-4-methoxyphenyl)((tert-butyldimethylsilyl) oxy)methyl)-2-oxo5,6-diphenylmorpholine-4-carboxylate

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