(S)-2-Amino-N-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(3-hydroxy-phenyl)-ethyl]-propionamide

Base Information

• Chemical Name: (S)-2-Amino-N-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(3-hydroxy-phenyl)-ethyl]-propionamide
• CAS No.: 167423-70-3
• Molecular Formula: C₁₇H₃₀N₂O₃Si
• Molecular Weight: 338.522
• Mol file: 167423-70-3.mol

Synonyms:(S)-2-Amino-N-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(3-hydroxy-phenyl)-ethyl]-propionamide

Chemical Property of (S)-2-Amino-N-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(3-hydroxy-phenyl)-ethyl]-propionamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-Amino-N-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(3-hydroxy-phenyl)-ethyl]-propionamide

There total 7 articles about (S)-2-Amino-N-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(3-hydroxy-phenyl)-ethyl]-propionamide 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%

{(S)-1-[(R)-1-(3-Allyloxy-phenyl)-2-(tert-butyl-dimethyl-silanyloxy)-ethylcarbamoyl]-ethyl}-carbamic acid allyl ester (167423-69-0) → (S)-2-Amino-N-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(3-hydroxy-phenyl)-ethyl]-propionamide (167423-70-3)

Guidance literature:

With lithium borohydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran;

DOI:10.1016/0040-4039(95)00449-M

Reference yield:

D-<2-<(tert-butyldimethylsilyl)oxy>-1-<3-(allyloxy)phenyl>ethyl>amine (169825-26-7) → (S)-2-Amino-N-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(3-hydroxy-phenyl)-ethyl]-propionamide (167423-70-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / EDC / CH₂Cl₂ / 2 h / Ambient temperature

2: LiBH₄, Pd(PPh₃)4 / tetrahydrofuran / 1 h / Ambient temperature

With lithium borohydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo961412m

Reference yield:

(2R,4R)-3-<2-azido-2-<3-(allyloxy)phenyl>-1-oxoethyl>-4-(phenylmethyl)-2-oxazolidinone (185112-18-9) → (S)-2-Amino-N-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(3-hydroxy-phenyl)-ethyl]-propionamide (167423-70-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 85.2 percent / LiOH, H₂O₂ / H₂O / 3 h / 0 °C

2: 100 percent

3: 93 percent / SnCl₂*2H₂O / methanol / 14 h / Ambient temperature

4: 100 percent / LiBH₄

5: 89 percent / Et₃N, DMAP / CH₂Cl₂ / 5 h / Ambient temperature

6: 88 percent / EDC / CH₂Cl₂ / 2 h / Ambient temperature

7: LiBH₄, Pd(PPh₃)4 / tetrahydrofuran / 1 h / Ambient temperature

With dmap; lithium hydroxide; lithium borohydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dihydrogen peroxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; tin(ll) chloride; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/jo961412m

upstream raw materials:

{(S)-1-[(R)-1-(3-Allyloxy-phenyl)-2-(tert-butyl-dimethyl-silanyloxy)-ethylcarbamoyl]-ethyl}-carbamic acid allyl ester

D-<2-<(tert-butyldimethylsilyl)oxy>-1-<3-(allyloxy)phenyl>ethyl>amine

(2R,4R)-3-<2-azido-2-<3-(allyloxy)phenyl>-1-oxoethyl>-4-(phenylmethyl)-2-oxazolidinone

(R)-2-(3-Allyloxy-phenyl)-2-amino-ethanol

Downstream raw materials:

{(R)-1-[(R)-1-{(S)-1-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(3-hydroxy-phenyl)-ethylcarbamoyl]-ethylcarbamoyl}-2-(4-fluoro-3-nitro-phenyl)-ethylcarbamoyl]-3-methyl-butyl}-methyl-carbamic acid tert-butyl ester