(4'S,5'R)-5,2',2',5'-Tetramethyl-4',5'-dihydro-[2,4']bioxazolyl-4,3'-dicarboxylic acid 3'-benzyl ester

Base Information

• Chemical Name: (4'S,5'R)-5,2',2',5'-Tetramethyl-4',5'-dihydro-[2,4']bioxazolyl-4,3'-dicarboxylic acid 3'-benzyl ester
• CAS No.: 670233-34-8
• Molecular Formula: C₁₉H₂₂N₂O₆
• Molecular Weight: 374.393
• Mol file: 670233-34-8.mol

Synonyms:(4'S,5'R)-5,2',2',5'-Tetramethyl-4',5'-dihydro-[2,4']bioxazolyl-4,3'-dicarboxylic acid 3'-benzyl ester

Chemical Property of (4'S,5'R)-5,2',2',5'-Tetramethyl-4',5'-dihydro-[2,4']bioxazolyl-4,3'-dicarboxylic acid 3'-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4'S,5'R)-5,2',2',5'-Tetramethyl-4',5'-dihydro-[2,4']bioxazolyl-4,3'-dicarboxylic acid 3'-benzyl ester

There total 5 articles about (4'S,5'R)-5,2',2',5'-Tetramethyl-4',5'-dihydro-[2,4']bioxazolyl-4,3'-dicarboxylic acid 3'-benzyl 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: 100.0%

(4'S,5'R)-5,2',2',5'-Tetramethyl-4',5'-dihydro-[2,4']bioxazolyl-4,3'-dicarboxylic acid 3'-benzyl ester 4-methyl ester (670233-33-7) → (4'S,5'R)-5,2',2',5'-Tetramethyl-4',5'-dihydro-[2,4']bioxazolyl-4,3'-dicarboxylic acid 3'-benzyl ester (670233-34-8)

Guidance literature:

With lithium hydroxide; In 1,4-dioxane; water;

DOI:10.1246/cl.2004.72

Reference yield:

(4S,5R)-3-((benzyloxy)carbonyl)-2,2,5-trimethyloxazolidine-4-carboxylic acid (160821-18-1) → (4'S,5'R)-5,2',2',5'-Tetramethyl-4',5'-dihydro-[2,4']bioxazolyl-4,3'-dicarboxylic acid 3'-benzyl ester (670233-34-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 92 percent / DCC; HOBt / dimethylformamide

2.1: MsCl; NEt₃ / CHCl₃

2.2: DBU / CHCl₃

3.1: NBS / tetrahydrofuran

3.2: Et₃N / tetrahydrofuran

4.1: Cs₂CO₃ / dioxane

5.1: 100 percent / LiOH / dioxane; H₂O

With lithium hydroxide; N-Bromosuccinimide; benzotriazol-1-ol; caesium carbonate; methanesulfonyl chloride; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; chloroform; water; N,N-dimethyl-formamide;

DOI:10.1246/cl.2004.72

Reference yield:

(4S,5R)-4-((Z)-1-Methoxycarbonyl-propenylcarbamoyl)-2,2,5-trimethyl-oxazolidine-3-carboxylic acid benzyl ester → (4'S,5'R)-5,2',2',5'-Tetramethyl-4',5'-dihydro-[2,4']bioxazolyl-4,3'-dicarboxylic acid 3'-benzyl ester (670233-34-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NBS / tetrahydrofuran

1.2: Et₃N / tetrahydrofuran

2.1: Cs₂CO₃ / dioxane

3.1: 100 percent / LiOH / dioxane; H₂O

With lithium hydroxide; N-Bromosuccinimide; caesium carbonate; In tetrahydrofuran; 1,4-dioxane; water;

DOI:10.1246/cl.2004.72

upstream raw materials:

(4'S,5'R)-5,2',2',5'-Tetramethyl-4',5'-dihydro-[2,4']bioxazolyl-4,3'-dicarboxylic acid 3'-benzyl ester 4-methyl ester

(4S,5R)-3-((benzyloxy)carbonyl)-2,2,5-trimethyloxazolidine-4-carboxylic acid

(4S,5R)-4-((1S,2R)-2-Hydroxy-1-methoxycarbonyl-propylcarbamoyl)-2,2,5-trimethyl-oxazolidine-3-carboxylic acid benzyl ester

(4S,5R)-4-((E)-2-Bromo-1-methoxycarbonyl-propenylcarbamoyl)-2,2,5-trimethyl-oxazolidine-3-carboxylic acid benzyl ester

Downstream raw materials:

C₅₅H₇₂N₈O₁₅SSi

(S)-2-{[2-((1S,2R)-1-Benzyloxycarbonylamino-2-hydroxy-propyl)-5-methyl-oxazole-4-carbonyl]-amino}-3-(tert-butyl-diphenyl-silanyloxy)-propionic acid methyl ester

(S)-2-{[2-((1S,2R)-1-Benzyloxycarbonylamino-2-hydroxy-propyl)-5-methyl-oxazole-4-carbonyl]-amino}-3-hydroxy-propionic acid methyl ester

(4'S,5'R)-4-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methoxycarbonyl-ethylcarbamoyl]-5,2',2',5'-tetramethyl-4',5'-dihydro-[2,4']bioxazolyl-3'-carboxylic acid benzyl ester