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

Base Information

Chemical Name:(2R,3S)-methyl 3-(3-bromo-4-methoxyphenyl)-3-((tert-butyldimethylsilyl)oxy)-2-(((1R,2S)-2-hydroxy-1,2-diphenylethyl)amino)propanoate
CAS No.:1352147-52-4
Molecular Formula:C₃₁H₄₀BrNO₅Si
Molecular Weight:614.652
Hs Code.:

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

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

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

There total 4 articles about (2R,3S)-methyl 3-(3-bromo-4-methoxyphenyl)-3-((tert-butyldimethylsilyl)oxy)-2-(((1R,2S)-2-hydroxy-1,2-diphenylethyl)amino)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: 90.0%

: 67-56-1
methanol

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

: 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

Guidance literature:: With zinc(II) chloride; In tetrahydrofuran; diethyl ether; at 80 ℃; for 24h; Inert atmosphere;
DOI:10.1016/j.tetlet.2011.11.069

Reference yield:

: 105228-46-4,335159-14-3
(5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

: 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

Guidance literature:: Multi-step reaction with 4 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

With palladium 10% on activated carbon; hydrogen; sodium hexamethyldisilazane; copper(II) bis(trifluoromethanesulfonate); zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; 2: Mukaiyama aldol reaction;
DOI:10.1016/j.tetlet.2011.11.069

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 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

Guidance literature:: Multi-step reaction with 4 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

With palladium 10% on activated carbon; hydrogen; sodium hexamethyldisilazane; copper(II) bis(trifluoromethanesulfonate); zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; 2: Mukaiyama aldol reaction;
DOI:10.1016/j.tetlet.2011.11.069