2',2'-dimethyl-4',5'-dihydro-[2,4']bioxazolyl-4,3'-dicarboxylic acid 4-benzyl ester 3'-tert-butyl ester

Base Information

• Chemical Name: 2',2'-dimethyl-4',5'-dihydro-[2,4']bioxazolyl-4,3'-dicarboxylic acid 4-benzyl ester 3'-tert-butyl ester
• CAS No.: 912656-68-9
• Molecular Formula: C₂₁H₂₆N₂O₆
• Molecular Weight: 402.447
• Mol file: 912656-68-9.mol

Synonyms:2',2'-dimethyl-4',5'-dihydro-[2,4']bioxazolyl-4,3'-dicarboxylic acid 4-benzyl ester 3'-tert-butyl ester

Chemical Property of 2',2'-dimethyl-4',5'-dihydro-[2,4']bioxazolyl-4,3'-dicarboxylic acid 4-benzyl ester 3'-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2',2'-dimethyl-4',5'-dihydro-[2,4']bioxazolyl-4,3'-dicarboxylic acid 4-benzyl ester 3'-tert-butyl ester

There total 2 articles about 2',2'-dimethyl-4',5'-dihydro-[2,4']bioxazolyl-4,3'-dicarboxylic acid 4-benzyl ester 3'-tert-butyl 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: 95.0%

(S)-2-[3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]oxazole-4-carboxylic acid (890403-75-5) + benzyl bromide (100-39-0) → 2',2'-dimethyl-4',5'-dihydro-[2,4']bioxazolyl-4,3'-dicarboxylic acid 4-benzyl ester 3'-tert-butyl ester (912656-68-9)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1021/ol061793i

Reference yield:

(S)-methyl 2-[3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]oxazole-4-carboxylate (203456-93-3) → 2',2'-dimethyl-4',5'-dihydro-[2,4']bioxazolyl-4,3'-dicarboxylic acid 4-benzyl ester 3'-tert-butyl ester (912656-68-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / LiOH*H₂O / methanol; tetrahydrofuran; H₂O / 3 h / 0 °C

2: 95 percent / K₂CO₃ / dimethylformamide / 12 h / 20 °C

With lithium hydroxide; potassium carbonate; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;

DOI:10.1021/ol061793i

Reference yield: 84.0%

(S)-2-[3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]oxazole-4-carboxylic acid (890403-75-5) + 2',2'-dimethyl-4',5'-dihydro-[2,4']bioxazolyl-4,3'-dicarboxylic acid 4-benzyl ester 3'-tert-butyl ester (912656-68-9) → (S)-4-[(S)-1-(4-Benzyloxycarbonyl-oxazol-2-yl)-2-hydroxy-ethylcarbamoyl]-2',2'-dimethyl-4',5'-dihydro-[2,4']bioxazolyl-3'-carboxylic acid tert-butyl ester (912656-49-6)

Guidance literature:

2',2'-dimethyl-4',5'-dihydro-[2,4']bioxazolyl-4,3'-dicarboxylic acid 4-benzyl ester 3'-tert-butyl ester; With hydrogenchloride; In 1,4-dioxane; ethyl acetate; at 20 ℃; for 1.5h;

(S)-2-[3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]oxazole-4-carboxylic acid; With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/ol061793i

upstream raw materials:

(S)-2-[3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]oxazole-4-carboxylic acid

benzyl bromide

(S)-methyl 2-[3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]oxazole-4-carboxylate

Downstream raw materials:

(S)-4-[(S)-1-(4-Benzyloxycarbonyl-oxazol-2-yl)-2-hydroxy-ethylcarbamoyl]-2',2'-dimethyl-4',5'-dihydro-[2,4']bioxazolyl-3'-carboxylic acid tert-butyl ester

2''',2'''-dimethyl-4''',5'''-dihydro-[2,4';2',4'';2'',4''']quateroxazole-4,3'''-dicarboxylic acid 4-benzyl ester 3'''-tert-butyl ester

telomestatin