4-(3-tert-butyl-1-oxo-dihydro-pyrrolo[1,2-c]oxazole-7a-carbonyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Base Information

• Chemical Name: 4-(3-tert-butyl-1-oxo-dihydro-pyrrolo[1,2-c]oxazole-7a-carbonyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester
• CAS No.: 433238-12-1
• Molecular Formula: C₂₄H₃₂N₂O₆
• Molecular Weight: 444.528

Synonyms:4-(3-tert-butyl-1-oxo-dihydro-pyrrolo[1,2-c]oxazole-7a-carbonyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Chemical Property of 4-(3-tert-butyl-1-oxo-dihydro-pyrrolo[1,2-c]oxazole-7a-carbonyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

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Technology Process of 4-(3-tert-butyl-1-oxo-dihydro-pyrrolo[1,2-c]oxazole-7a-carbonyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

There total 3 articles about 4-(3-tert-butyl-1-oxo-dihydro-pyrrolo[1,2-c]oxazole-7a-carbonyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid 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: 89.0%

(R)-4-[(R)-((3R,7aR)-3-tert-Butyl-1-oxo-dihydro-pyrrolo[1,2-c]oxazol-7a-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester (433235-59-7) → 4-(3-tert-butyl-1-oxo-dihydro-pyrrolo[1,2-c]oxazole-7a-carbonyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester (433238-12-1)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 0 ℃;

DOI:10.1016/S0040-4039(01)02254-7

Reference yield:

(4R)-4-formyl-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester (133464-37-6) → 4-(3-tert-butyl-1-oxo-dihydro-pyrrolo[1,2-c]oxazole-7a-carbonyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester (433238-12-1)

Guidance literature:

Multi-step reaction with 2 steps

1: LDA / tetrahydrofuran / -78 °C

2: 89 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 °C

With Dess-Martin periodane; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(01)02254-7

Reference yield:

(2R,5S)-2-tert-butyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one (81286-82-0) → 4-(3-tert-butyl-1-oxo-dihydro-pyrrolo[1,2-c]oxazole-7a-carbonyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester (433238-12-1)

Guidance literature:

Multi-step reaction with 2 steps

1: LDA / tetrahydrofuran / -78 °C

2: 89 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 °C

With Dess-Martin periodane; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(01)02254-7

upstream raw materials:

(R)-4-[(R)-((3R,7aR)-3-tert-Butyl-1-oxo-dihydro-pyrrolo[1,2-c]oxazol-7a-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

(4R)-4-formyl-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester

(2R,5S)-2-tert-butyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one

Downstream raw materials:

(R)-4-[(S)-((3R,7aR)-3-tert-Butyl-1-oxo-dihydro-pyrrolo[1,2-c]oxazol-7a-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

(2R,5R)-2-[(1S,2R)-2-Benzyloxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-1-trimethylsilanyloxy-propyl]-5-[(S)-2-benzyloxycarbonyl-2-(4-benzyloxy-3,5-dichloro-benzoylamino)-ethyl]-1-hydroxy-pyrrolidine-2-carboxylic acid benzyl ester

(2R,5R)-2-[(1S,2R)-2-Benzyloxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-1-trimethylsilanyloxy-propyl]-5-[(R)-2-benzyloxycarbonyl-2-(4-benzyloxy-3,5-dichloro-benzoylamino)-ethyl]-1-hydroxy-pyrrolidine-2-carboxylic acid benzyl ester

(2R,5R)-2-[(1S,2R)-2-Benzyloxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-1-trimethylsilanyloxy-propyl]-5-[(S)-2-benzyloxycarbonyl-2-(4-benzyloxy-3,5-dichloro-benzoylamino)-ethyl]-pyrrolidine-2-carboxylic acid benzyl ester

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