(S)-2-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-propionylamino]-3-hydroxy-propionic acid methyl ester

Base Information

• Chemical Name: (S)-2-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-propionylamino]-3-hydroxy-propionic acid methyl ester
• CAS No.: 187460-14-6
• Molecular Formula: C₂₃H₃₁NO₅Si
• Molecular Weight: 429.588

Synonyms:(S)-2-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-propionylamino]-3-hydroxy-propionic acid methyl ester

Chemical Property of (S)-2-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-propionylamino]-3-hydroxy-propionic acid methyl ester

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Technology Process of (S)-2-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-propionylamino]-3-hydroxy-propionic acid methyl ester

There total 2 articles about (S)-2-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-propionylamino]-3-hydroxy-propionic acid methyl ester 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: 81.0%

methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride (5680-80-8) + (S)-2-[(1,1-dimethylethyl)diphenylsilyl]oxypropanoic acid (125941-75-5) → (S)-2-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-propionylamino]-3-hydroxy-propionic acid methyl ester (187460-14-6)

Guidance literature:

With 4-methyl-morpholine; diethyl cyanophosphonate; In N,N-dimethyl-formamide; for 40h; Ambient temperature;

DOI:10.1055/s-1997-17829

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (S)-2-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-propionylamino]-3-hydroxy-propionic acid methyl ester (187460-14-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / imidazole / dimethylformamide / 48 h / Ambient temperature

2: 81 percent / (EtO)2P(O)CN, N-methylmorpholine / dimethylformamide / 40 h / Ambient temperature

With 4-methyl-morpholine; 1H-imidazole; diethyl cyanophosphonate; In N,N-dimethyl-formamide;

DOI:10.1055/s-1997-17829

Reference yield:

(S)-2-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-propionylamino]-3-hydroxy-propionic acid methyl ester (187460-14-6) → (R)-2-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-propionylamino]-3-chloro-propionic acid methyl ester (187460-15-7)

Guidance literature:

With thionyl chloride; In tetrahydrofuran; at 4 ℃; Yield given;

DOI:10.1055/s-1997-17829

upstream raw materials:

methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride

(S)-2-[(1,1-dimethylethyl)diphenylsilyl]oxypropanoic acid

tert-butylchlorodiphenylsilane

Downstream raw materials:

(R)-2-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-propionylamino]-3-chloro-propionic acid methyl ester

2-[(S)-1-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-oxazole-4-carbaldehyde

{2-[(S)-1-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-oxazol-4-yl}-methanol

2-[(S)-1-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-oxazole-4-carboxylic acid methyl ester

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