methyl (2S)-3-{4'-[(tert-butyldimethylsilyl)oxy]phenyl}-2-[(1'',5''-dimethoxybenzyl)amino]propanoate

Base Information

Chemical Name:methyl (2S)-3-{4'-[(tert-butyldimethylsilyl)oxy]phenyl}-2-[(1'',5''-dimethoxybenzyl)amino]propanoate
CAS No.:1257082-97-5
Molecular Formula:C₂₅H₃₇NO₅Si
Molecular Weight:459.658
Hs Code.:

Synonyms:methyl (2S)-3-{4'-[(tert-butyldimethylsilyl)oxy]phenyl}-2-[(1'',5''-dimethoxybenzyl)amino]propanoate

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Chemical Property of methyl (2S)-3-{4'-[(tert-butyldimethylsilyl)oxy]phenyl}-2-[(1'',5''-dimethoxybenzyl)amino]propanoate

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Technology Process of methyl (2S)-3-{4'-[(tert-butyldimethylsilyl)oxy]phenyl}-2-[(1'',5''-dimethoxybenzyl)amino]propanoate

There total 3 articles about methyl (2S)-3-{4'-[(tert-butyldimethylsilyl)oxy]phenyl}-2-[(1'',5''-dimethoxybenzyl)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: 83.0%

: 613-45-6
2,4-Dimethoxybenzaldehyde

: 216974-09-3
methyl (2S)-2-amino-3-{4'-[(tert-butyldimethylsilyl)oxy]phenyl}propanoate

: 1257082-97-5
methyl (2S)-3-{4'-[(tert-butyldimethylsilyl)oxy]phenyl}-2-[(1'',5''-dimethoxybenzyl)amino]propanoate

Guidance literature:: With sodium cyanoborohydride; acetic acid; In methanol; at 20 ℃; for 2h; Inert atmosphere;
DOI:10.1002/ejoc.201000597

Reference yield:

: 613-45-6
2,4-Dimethoxybenzaldehyde

: 216974-09-3
methyl (2S)-2-amino-3-{4'-[(tert-butyldimethylsilyl)oxy]phenyl}propanoate

: 1257082-97-5
methyl (2S)-3-{4'-[(tert-butyldimethylsilyl)oxy]phenyl}-2-[(1'',5''-dimethoxybenzyl)amino]propanoate

: methyl (2R)-3-{4'-[(tert-butyldimethylsilyl)oxy]phenyl}-2-[(1'',5''-dimethoxybenzyl)amino]propanoate

Guidance literature:: With sodium cyanoborohydride; acetic acid; In methanol; at 25 ℃; Reagent/catalyst; Overall yield = 58 percent; Optical yield = 85 percent ee;
DOI:10.1021/acs.orglett.0c00431

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1257082-97-5
methyl (2S)-3-{4'-[(tert-butyldimethylsilyl)oxy]phenyl}-2-[(1'',5''-dimethoxybenzyl)amino]propanoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 1H-imidazole / dichloromethane / 19 h / 20 °C

2.1: acetic acid / methanol / 0.5 h / 20 °C

2.2: 1.5 h / 20 °C

With 1H-imidazole; acetic acid; In methanol; dichloromethane;
DOI:10.1021/acs.joc.8b01530