(2S,3S)-3-Acetoxy-2-tert-butoxycarbonylamino-3-[4-methoxy-3-(3-methyl-but-2-enyl)-phenyl]-propionic acid

Base Information

Chemical Name:(2S,3S)-3-Acetoxy-2-tert-butoxycarbonylamino-3-[4-methoxy-3-(3-methyl-but-2-enyl)-phenyl]-propionic acid
CAS No.:187400-10-8
Molecular Formula:C₂₂H₃₁NO₇
Molecular Weight:421.491
Hs Code.:

Synonyms:(2S,3S)-3-Acetoxy-2-tert-butoxycarbonylamino-3-[4-methoxy-3-(3-methyl-but-2-enyl)-phenyl]-propionic acid

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Chemical Property of (2S,3S)-3-Acetoxy-2-tert-butoxycarbonylamino-3-[4-methoxy-3-(3-methyl-but-2-enyl)-phenyl]-propionic acid

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Technology Process of (2S,3S)-3-Acetoxy-2-tert-butoxycarbonylamino-3-[4-methoxy-3-(3-methyl-but-2-enyl)-phenyl]-propionic acid

There total 9 articles about (2S,3S)-3-Acetoxy-2-tert-butoxycarbonylamino-3-[4-methoxy-3-(3-methyl-but-2-enyl)-phenyl]-propionic acid 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: 70.0%

: 187400-09-5
Acetic acid (1S,2R)-2-tert-butoxycarbonylamino-3-hydroxy-1-[4-methoxy-3-(3-methyl-but-2-enyl)-phenyl]-propyl ester

: 187400-10-8
(2S,3S)-3-Acetoxy-2-tert-butoxycarbonylamino-3-[4-methoxy-3-(3-methyl-but-2-enyl)-phenyl]-propionic acid

Guidance literature:: With dipyridinium dichromate; In N,N-dimethyl-formamide; for 10h; Ambient temperature;
DOI:10.1016/S0040-4039(96)02298-8

Reference yield:

: 106-41-2
4-bromo-phenol

: 187400-10-8
(2S,3S)-3-Acetoxy-2-tert-butoxycarbonylamino-3-[4-methoxy-3-(3-methyl-but-2-enyl)-phenyl]-propionic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 56 percent / 1.) Na / benzene / 1.) reflux 8 h; 2.) rt., 24 h

2: 95 percent / K₂CO₃ / acetone / 2 h / Heating

3: 72 percent / 1.) Mg / tetrahydrofuran / 0 - 25 °C

4: DMAP, pyridine

5: 69 percent / 80percent aq. AcOH / 12 h / Ambient temperature

6: 70 percent / PDC / dimethylformamide / 10 h / Ambient temperature

With pyridine; dmap; dipyridinium dichromate; sodium; potassium carbonate; magnesium; acetic acid; In tetrahydrofuran; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1016/S0040-4039(96)02298-8

Reference yield:

: 151071-00-0
4-bromo-2-(3-methylbut-2-en-1-yl)phenol

: 187400-10-8
(2S,3S)-3-Acetoxy-2-tert-butoxycarbonylamino-3-[4-methoxy-3-(3-methyl-but-2-enyl)-phenyl]-propionic acid

Guidance literature:: Multi-step reaction with 5 steps

1: 95 percent / K₂CO₃ / acetone / 2 h / Heating

2: 72 percent / 1.) Mg / tetrahydrofuran / 0 - 25 °C

3: DMAP, pyridine

4: 69 percent / 80percent aq. AcOH / 12 h / Ambient temperature

5: 70 percent / PDC / dimethylformamide / 10 h / Ambient temperature

With pyridine; dmap; dipyridinium dichromate; potassium carbonate; magnesium; acetic acid; In tetrahydrofuran; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0040-4039(96)02298-8