(2S,3S)-3-(4-Benzyloxy-phenyl)-2-(tert-butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid

Base Information

Chemical Name:(2S,3S)-3-(4-Benzyloxy-phenyl)-2-(tert-butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid
CAS No.:188446-32-4
Molecular Formula:C₂₈H₄₁NO₆Si
Molecular Weight:515.722
Hs Code.:

Synonyms:(2S,3S)-3-(4-Benzyloxy-phenyl)-2-(tert-butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid

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Chemical Property of (2S,3S)-3-(4-Benzyloxy-phenyl)-2-(tert-butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid

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Technology Process of (2S,3S)-3-(4-Benzyloxy-phenyl)-2-(tert-butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid

There total 7 articles about (2S,3S)-3-(4-Benzyloxy-phenyl)-2-(tert-butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-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: 40.0%

: 188446-31-3
(2S,3S)-3-(4-Benzyloxy-phenyl)-2-tert-butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid

: 74-88-4
methyl iodide

: 188446-32-4
(2S,3S)-3-(4-Benzyloxy-phenyl)-2-(tert-butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid

Guidance literature:: With sodium hydride; In tetrahydrofuran; at -20 - 25 ℃; for 7h;
DOI:10.1021/jo961346o

Reference yield:

: 4397-53-9
p-benzyloxybenzaldehyde

: 188446-32-4
(2S,3S)-3-(4-Benzyloxy-phenyl)-2-(tert-butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid

Guidance literature:: Multi-step reaction with 6 steps

1: n-BuLi / tetrahydrofuran / 1.5 h / -78 - -30 °C

2: 1.) 0.25N HCl, 2.) NaHCO₃ / 2.) H₂O

3: 86 percent / Et₃N / CH₂Cl₂ / 24 h / -10 - 4 °C

4: 83 percent / K₂CO₃ / tetrahydrofuran; H₂O / 3 h / 25 °C

5: 95 percent / LiOH / 2-methyl-propan-2-ol; H₂O / 4.5 h / 5 - 25 °C

6: 40 percent / NaH / tetrahydrofuran / 7 h / -20 - 25 °C

With hydrogenchloride; lithium hydroxide; n-butyllithium; sodium hydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/jo961346o

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 188446-32-4
(2S,3S)-3-(4-Benzyloxy-phenyl)-2-(tert-butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid

Guidance literature:: Multi-step reaction with 4 steps

1: 86 percent / Et₃N / CH₂Cl₂ / 24 h / -10 - 4 °C

2: 83 percent / K₂CO₃ / tetrahydrofuran; H₂O / 3 h / 25 °C

3: 95 percent / LiOH / 2-methyl-propan-2-ol; H₂O / 4.5 h / 5 - 25 °C

4: 40 percent / NaH / tetrahydrofuran / 7 h / -20 - 25 °C

With lithium hydroxide; sodium hydride; potassium carbonate; triethylamine; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/jo961346o