2-[(S)-1-{[2''-(tert-butoxycarbonylaminomethyl)[2,4':2';4'']teroxazole-4-carbothioyl]amino}-2-(tert-butyldimethylsilanyloxy)ethyl]-5-phenyloxazole-4-carboxylic acid methyl ester

Base Information

• Chemical Name: 2-[(S)-1-{[2''-(tert-butoxycarbonylaminomethyl)[2,4':2';4'']teroxazole-4-carbothioyl]amino}-2-(tert-butyldimethylsilanyloxy)ethyl]-5-phenyloxazole-4-carboxylic acid methyl ester
• CAS No.: 848761-06-8
• Molecular Formula: C₃₅H₄₂N₆O₉SSi
• Molecular Weight: 750.905
• Mol file: 848761-06-8.mol

Synonyms:2-[(S)-1-{[2''-(tert-butoxycarbonylaminomethyl)[2,4':2';4'']teroxazole-4-carbothioyl]amino}-2-(tert-butyldimethylsilanyloxy)ethyl]-5-phenyloxazole-4-carboxylic acid methyl ester

Chemical Property of 2-[(S)-1-{[2''-(tert-butoxycarbonylaminomethyl)[2,4':2';4'']teroxazole-4-carbothioyl]amino}-2-(tert-butyldimethylsilanyloxy)ethyl]-5-phenyloxazole-4-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(S)-1-{[2''-(tert-butoxycarbonylaminomethyl)[2,4':2';4'']teroxazole-4-carbothioyl]amino}-2-(tert-butyldimethylsilanyloxy)ethyl]-5-phenyloxazole-4-carboxylic acid methyl ester

There total 8 articles about 2-[(S)-1-{[2''-(tert-butoxycarbonylaminomethyl)[2,4':2';4'']teroxazole-4-carbothioyl]amino}-2-(tert-butyldimethylsilanyloxy)ethyl]-5-phenyloxazole-4-carboxylic 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: 50.0%

2-[(S)-1-{[2''-(tert-butoxycarbonylaminomethyl)[2,4':2';4'']teroxazole-4-carbonyl]amino}-2-(tert-butyldimethylsilanyloxy)ethyl]-5-phenyloxazole-4-carboxylic acid methyl ester (848761-05-7) → 2-[(S)-1-{[2''-(tert-butoxycarbonylaminomethyl)[2,4':2';4'']teroxazole-4-carbothioyl]amino}-2-(tert-butyldimethylsilanyloxy)ethyl]-5-phenyloxazole-4-carboxylic acid methyl ester (848761-06-8)

Guidance literature:

With Lawessons reagent; In tetrahydrofuran; for 18h; Heating;

DOI:10.1039/b416530f

Reference yield:

2-((S)-2-benzyloxy-1-{[2-(tert-butoxycarbonylaminomethyl)oxazole-4-carbonyl]amino}ethyl)oxazole-4-carboxylic acid methyl ester (848761-02-4) → 2-[(S)-1-{[2''-(tert-butoxycarbonylaminomethyl)[2,4':2';4'']teroxazole-4-carbothioyl]amino}-2-(tert-butyldimethylsilanyloxy)ethyl]-5-phenyloxazole-4-carboxylic acid methyl ester (848761-06-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 81 percent / H₂ / Pd(OH)2/C / methanol; tetrahydrofuran / 20 °C

2.1: (diethylamino)sulfur trifluoride / CH₂Cl₂ / 1.5 h / -78 °C

2.2: 57 percent / BrCCl₃; DBU / CH₂Cl₂ / 24 h / 0 - 20 °C

3.1: 88 percent / aq. NaOH / tetrahydrofuran / 24 h / 20 °C

4.1: 87 percent / 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide*HCl; 1-hydroxybenzotriazole; 4-methylmorpholine / CH₂Cl₂ / 24 h / 0 - 20 °C

5.1: 50 percent / Lawesson's reagent / tetrahydrofuran / 18 h / Heating

With Lawessons reagent; 4-methyl-morpholine; sodium hydroxide; diethylamino-sulfur trifluoride; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1039/b416530f

Reference yield:

(S)-2-benzyloxy-1-(4-methoxycarbonyloxazol-2-yl)ethylammonium chloride (848761-00-2) → 2-[(S)-1-{[2''-(tert-butoxycarbonylaminomethyl)[2,4':2';4'']teroxazole-4-carbothioyl]amino}-2-(tert-butyldimethylsilanyloxy)ethyl]-5-phenyloxazole-4-carboxylic acid methyl ester (848761-06-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 56 percent / 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide*HCl; 1-hydroxybenzotriazole; 4-methylmorpholine / CH₂Cl₂ / 24 h / 0 - 20 °C

2.1: 81 percent / H₂ / Pd(OH)2/C / methanol; tetrahydrofuran / 20 °C

3.1: (diethylamino)sulfur trifluoride / CH₂Cl₂ / 1.5 h / -78 °C

3.2: 57 percent / BrCCl₃; DBU / CH₂Cl₂ / 24 h / 0 - 20 °C

4.1: 88 percent / aq. NaOH / tetrahydrofuran / 24 h / 20 °C

5.1: 87 percent / 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide*HCl; 1-hydroxybenzotriazole; 4-methylmorpholine / CH₂Cl₂ / 24 h / 0 - 20 °C

6.1: 50 percent / Lawesson's reagent / tetrahydrofuran / 18 h / Heating

With Lawessons reagent; 4-methyl-morpholine; sodium hydroxide; diethylamino-sulfur trifluoride; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1039/b416530f

upstream raw materials:

2-[(S)-1-{[2''-(tert-butoxycarbonylaminomethyl)[2,4':2';4'']teroxazole-4-carbonyl]amino}-2-(tert-butyldimethylsilanyloxy)ethyl]-5-phenyloxazole-4-carboxylic acid methyl ester

2''-(tert-butoxycarbonylaminomethyl)[2,4';2',4'']teroxazole-4-carboxylic acid

2''-(tert-butoxycarbonylaminomethyl)[2,4';2',4'']teroxazole-4-carboxylic acid methyl ester

2-((S)-1-{[2-(tert-butoxycarbonylaminomethyl)oxazole-4-carbonyl]amino}-2-hydroxyethyl)oxazole-4-carboxylic acid methyl ester

Downstream raw materials:

C₂₉H₂₈N₆O₉S

2-{(S)-1-[(2-{[(R)-1-((2S,3S)-2-tert-butoxycarbonylamino-3-methylpentanoylamino)-2-methylpropylamino]methyl}[2,4';2',4]teroxazole-4-carbothioyl)amino]-2-hydroxyethyl}-5-phenyloxazole-4-carboxylic acid methyl ester

2-{(S)-1-[(2''-{[(S)-1-((2S,3S)-2-tert-butoxycarbonylamino-3-methylpentanoylamino)-2-methylpropylamino]methyl}[2,4';2',4'']teroxazole-4-carbothioyl)amino]-2-hydroxyethyl}-5-phenyloxazole-4-carboxylic acid methyl ester

C₃₄H₃₆N₈O₈S