2-Benzyloxycarbonylamino-N-((S)-2-oxo-tetrahydro-furan-3-yl)-malonamic acid tert-butyl ester

Base Information

• Chemical Name: 2-Benzyloxycarbonylamino-N-((S)-2-oxo-tetrahydro-furan-3-yl)-malonamic acid tert-butyl ester
• CAS No.: 84245-58-9
• Molecular Formula: C₁₉H₂₄N₂O₇
• Molecular Weight: 392.409
• Mol file: 84245-58-9.mol

Synonyms:2-Benzyloxycarbonylamino-N-((S)-2-oxo-tetrahydro-furan-3-yl)-malonamic acid tert-butyl ester

Chemical Property of 2-Benzyloxycarbonylamino-N-((S)-2-oxo-tetrahydro-furan-3-yl)-malonamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Benzyloxycarbonylamino-N-((S)-2-oxo-tetrahydro-furan-3-yl)-malonamic acid tert-butyl ester

There total 1 articles about 2-Benzyloxycarbonylamino-N-((S)-2-oxo-tetrahydro-furan-3-yl)-malonamic acid 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: 82.0%

mono-t-butyl ester of N-benzyloxycarbonylaminomalonic acid (84245-57-8) + L-homoserine lactone (2185-02-6) → 2-Benzyloxycarbonylamino-N-((S)-2-oxo-tetrahydro-furan-3-yl)-malonamic acid tert-butyl ester (84245-58-9)

Guidance literature:

With dicyclohexyl-carbodiimide; In tert-butyl alcohol;

DOI:10.1016/S0040-4039(00)87699-6

Reference yield:

2-Benzyloxycarbonylamino-N-((S)-2-oxo-tetrahydro-furan-3-yl)-malonamic acid tert-butyl ester (84245-58-9) → LL-3-amino-2-piperidone-6-carboxylic acid (LL-Acp) (84278-06-8,247112-91-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / H₂ / Pd

2: 1.) (C₆H₅O)3PCH₃I, 2.)tetramethylguanidine

3: 38 percent / Cu / quinoline / 3 h / 210 °C / scrupulously dried solvent

4: 1.) HCl, 2.) AgO / 1.) 25 deg C, 3 h

5: optical purity 95percent (established via Boc-L-Phe-Acp-OEt derivative)

With hydrogenchloride; silver(II) oxide; 1,1,3,3-tetramethylguanidine; methyltriphenoxyphosphonium iodide; hydrogen; copper; palladium; In quinoline;

DOI:10.1016/S0040-4039(00)87699-6

Reference yield:

2-Benzyloxycarbonylamino-N-((S)-2-oxo-tetrahydro-furan-3-yl)-malonamic acid tert-butyl ester (84245-58-9) → (2R,5R)-5-Amino-6-oxo-piperidine-2-carboxylic acid (42155-72-6,42155-74-8,84278-06-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / H₂ / Pd

2: 1.) (C₆H₅O)3PCH₃I, 2.)tetramethylguanidine

3: 38 percent / Cu / quinoline / 3 h / 210 °C / scrupulously dried solvent

4: 1.) HCl, 2.) AgO / 1.) 25 deg C, 3 h

5: optical purity 95percent (established via Boc-L-Phe-Acp-OEt derivative)

With hydrogenchloride; silver(II) oxide; 1,1,3,3-tetramethylguanidine; methyltriphenoxyphosphonium iodide; hydrogen; copper; palladium; In quinoline;

DOI:10.1016/S0040-4039(00)87699-6

upstream raw materials:

mono-t-butyl ester of N-benzyloxycarbonylaminomalonic acid

L-homoserine lactone

Downstream raw materials:

(1S,4S)-2,5-Diaza-bicyclo[2.2.2]octane-3,6-dione

LL-3-amino-2-piperidone-6-carboxylic acid (LL-Acp)

(2R,5R)-5-Amino-6-oxo-piperidine-2-carboxylic acid