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

Base Information

Chemical Name:(2R,3S)-methyl 2-amino-3-(3-bromo-4-methoxyphenyl)-3-((tert-butyldimethylsilyl)oxy)propanoate
CAS No.:1352147-55-7
Molecular Formula:C₁₇H₂₈BrNO₄Si
Molecular Weight:418.403
Hs Code.:

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

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

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

There total 5 articles about (2R,3S)-methyl 2-amino-3-(3-bromo-4-methoxyphenyl)-3-((tert-butyldimethylsilyl)oxy)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: 79.0%

: 1352147-52-4
(2R,3S)-methyl 3-(3-bromo-4-methoxyphenyl)-3-((tert-butyldimethylsilyl)oxy)-2-(((1R,2S)-2-hydroxy-1,2-diphenylethyl)amino)propanoate

: 1352147-55-7
(2R,3S)-methyl 2-amino-3-(3-bromo-4-methoxyphenyl)-3-((tert-butyldimethylsilyl)oxy)propanoate

Guidance literature:: (2R,3S)-methyl 3-(3-bromo-4-methoxyphenyl)-3-((tert-butyldimethylsilyl)oxy)-2-(((1R,2S)-2-hydroxy-1,2-diphenylethyl)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:

: 1352147-49-9
(3R,5R,6S)-3-((S)-(3-bromo-4-methoxyphenyl)((tert-butyldimethylsilyl)oxy)methyl)-5,6-diphenylmorpholin-2-one

: 1352147-55-7
(2R,3S)-methyl 2-amino-3-(3-bromo-4-methoxyphenyl)-3-((tert-butyldimethylsilyl)oxy)propanoate

Guidance literature:: Multi-step reaction with 2 steps

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

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

With lead(IV) tetraacetate; zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;
DOI:10.1016/j.tetlet.2011.11.069

Reference yield:

: 911319-41-0
benzyl (2S,3R)-(+)-6-tert-butyldimethylsilyloxy-2,3-diphenyl-4-morpholin-5-enecarboxylate

: 1352147-55-7
(2R,3S)-methyl 2-amino-3-(3-bromo-4-methoxyphenyl)-3-((tert-butyldimethylsilyl)oxy)propanoate

Guidance literature:: Multi-step reaction with 4 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: 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); zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; acetonitrile; 1: Mukaiyama aldol reaction;
DOI:10.1016/j.tetlet.2011.11.069