(4S)-2-(3-benzyloxycarbonyl-2,2-dimethyloxazolidin-4-ylmethyl)malonic acid di-tert-butyl ester

Base Information

• Chemical Name: (4S)-2-(3-benzyloxycarbonyl-2,2-dimethyloxazolidin-4-ylmethyl)malonic acid di-tert-butyl ester
• CAS No.: 912354-29-1
• Molecular Formula: C₂₅H₃₇NO₇
• Molecular Weight: 463.571
• Mol file: 912354-29-1.mol

Synonyms:(4S)-2-(3-benzyloxycarbonyl-2,2-dimethyloxazolidin-4-ylmethyl)malonic acid di-tert-butyl ester

Chemical Property of (4S)-2-(3-benzyloxycarbonyl-2,2-dimethyloxazolidin-4-ylmethyl)malonic acid di-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-2-(3-benzyloxycarbonyl-2,2-dimethyloxazolidin-4-ylmethyl)malonic acid di-tert-butyl ester

There total 3 articles about (4S)-2-(3-benzyloxycarbonyl-2,2-dimethyloxazolidin-4-ylmethyl)malonic acid di-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: 90.0%

2S-(3-benzyloxycarbonyl-2,2-dimethyloxazolidin-4-ylmethylene)-malonic acid di-tert-butyl ester (873310-64-6) → (4S)-2-(3-benzyloxycarbonyl-2,2-dimethyloxazolidin-4-ylmethyl)malonic acid di-tert-butyl ester (912354-29-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol;

DOI:10.1021/jo061037q

Reference yield:

(4R)-4-formyl-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester (133464-37-6) → (4S)-2-(3-benzyloxycarbonyl-2,2-dimethyloxazolidin-4-ylmethyl)malonic acid di-tert-butyl ester (912354-29-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: LDA; HMPA / tetrahydrofuran / -78 °C

1.2: 80 percent / Ac₂O; DMAP; pyridine

2.1: 90 percent / H₂ / Pd/C / methanol

With N,N,N,N,N,N-hexamethylphosphoric triamide; hydrogen; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol;

DOI:10.1021/jo061037q

Reference yield:

(S)-hydroxymethyl-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester (133464-36-5) → (4S)-2-(3-benzyloxycarbonyl-2,2-dimethyloxazolidin-4-ylmethyl)malonic acid di-tert-butyl ester (912354-29-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 90 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

2.1: LDA; HMPA / tetrahydrofuran / -78 °C

2.2: 80 percent / Ac₂O; DMAP; pyridine

3.1: 90 percent / H₂ / Pd/C / methanol

With N,N,N,N,N,N-hexamethylphosphoric triamide; oxalyl dichloride; hydrogen; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; 1.1: Swern oxidation;

DOI:10.1021/jo061037q

upstream raw materials:

2S-(3-benzyloxycarbonyl-2,2-dimethyloxazolidin-4-ylmethylene)-malonic acid di-tert-butyl ester

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

(S)-hydroxymethyl-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester

Downstream raw materials:

N-α-(9-fluorenylmethoxycarbonyl)-L-γ-carboxy-glutamic acid-γ,γ-tert-butyl ester

N-(benzyloxycarbonyl)-γ,γ-di-tert-butyl-L-γ-carboxyglutamic acid

(2S)-benzyloxycarbonylamino-4,4-bis-tert-butyloxycarbonylhexanedioic acid 6-tert-butyl ester

(5S)-benzyloxycarbonylamino-3,3-bis-tert-butyloxycarbonyl-6-hydroxyhexanoic acid tert-butyl ester