4-Oxazolecarboxylic acid, 2-[(1S)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-[[(phenylmethoxy)carb onyl]amino]ethyl]-

Base Information

• Chemical Name: 4-Oxazolecarboxylic acid, 2-[(1S)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-[[(phenylmethoxy)carb onyl]amino]ethyl]-
• CAS No.: 915094-65-4
• Molecular Formula: C20H28N2O6Si
• Molecular Weight: 420.538
• Mol file: 915094-65-4.mol

Synonyms:

Chemical Property of 4-Oxazolecarboxylic acid, 2-[(1S)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-[[(phenylmethoxy)carb onyl]amino]ethyl]-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Oxazolecarboxylic acid, 2-[(1S)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-[[(phenylmethoxy)carb onyl]amino]ethyl]-

There total 5 articles about 4-Oxazolecarboxylic acid, 2-[(1S)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-[[(phenylmethoxy)carb onyl]amino]ethyl]- 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: 82.0%

2-[(S)-1-benzyloxycarbonylamino-2-(tert-butyldimethylsilanyloxy)ethyl]oxazole-4-carboxylic acid methyl ester (915094-64-3) → 2-[(S)-1-benzyloxycarbonylamino-2-(tert-butyldimethylsilanyloxy)ethyl]oxazole-4-carboxylic acid (915094-65-4)

Guidance literature:

With sodium hydroxide; water; In tetrahydrofuran; at 20 ℃; for 18h;

DOI:10.1039/b802477d

Reference yield:

(S)-2-[(S)-2-benzyloxycarbonylamino-3-(tert-butyldimethylsilanyloxy)propionylamino]-3-hydroxypropionic acid methyl ester (915094-63-2) → 2-[(S)-1-benzyloxycarbonylamino-2-(tert-butyldimethylsilanyloxy)ethyl]oxazole-4-carboxylic acid (915094-65-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: DAST / CH₂Cl₂ / 0.17 h

1.2: 77 percent / DBU; BrCCl₃ / CH₂Cl₂ / 1.5 h / 20 °C

2.1: LiOH / tetrahydrofuran; H₂O / 1 h / 20 °C

With lithium hydroxide; 4,4'-diaminostilbene-2,2'-disulfonic acid; In tetrahydrofuran; dichloromethane; water;

DOI:10.3987/com-06-s(o)38

Reference yield:

(S)-2-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid (104499-27-6,146346-84-1) → 2-[(S)-1-benzyloxycarbonylamino-2-(tert-butyldimethylsilanyloxy)ethyl]oxazole-4-carboxylic acid (915094-65-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: EDCI; HOBt; Et₃N

2.1: DAST / CH₂Cl₂ / 0.17 h

2.2: 77 percent / DBU; BrCCl₃ / CH₂Cl₂ / 1.5 h / 20 °C

3.1: LiOH / tetrahydrofuran; H₂O / 1 h / 20 °C

With lithium hydroxide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 4,4'-diaminostilbene-2,2'-disulfonic acid; In tetrahydrofuran; dichloromethane; water;

DOI:10.3987/com-06-s(o)38

upstream raw materials:

2-[(S)-1-benzyloxycarbonylamino-2-(tert-butyldimethylsilanyloxy)ethyl]oxazole-4-carboxylic acid methyl ester

(S)-2-[(S)-2-benzyloxycarbonylamino-3-(tert-butyldimethylsilanyloxy)propionylamino]-3-hydroxypropionic acid methyl ester

N-(benzyloxycarbonyl)-L-serine

(S)-2-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid

Downstream raw materials:

2''-[(S)-1-benzyloxycarbonylamino-2-(tert-butyldimethylsilanyloxy)ethyl][2,4';2',4'']teroxazole-4-carboxylic acid methyl ester

C₂₆H₃₀N₄O₈Si

2-((S)-1-benzyloxycarbonylamino-2-hydroxyethyl)oxazole-4-carboxylic acid