N-<4-(N-Cbz-D,L-erythro,threo-5-oxo-4-oxazolidinyl)-2-fluoropropionyl>-L-glutamic acid di-tert-butyl ester

Base Information

• Chemical Name: N-<4-(N-Cbz-D,L-erythro,threo-5-oxo-4-oxazolidinyl)-2-fluoropropionyl>-L-glutamic acid di-tert-butyl ester
• CAS No.: 124688-46-6
• Molecular Formula: C₂₇H₃₇FN₂O₉
• Molecular Weight: 552.597
• Mol file: 124688-46-6.mol

Synonyms:

Chemical Property of N-<4-(N-Cbz-D,L-erythro,threo-5-oxo-4-oxazolidinyl)-2-fluoropropionyl>-L-glutamic acid di-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-<4-(N-Cbz-D,L-erythro,threo-5-oxo-4-oxazolidinyl)-2-fluoropropionyl>-L-glutamic acid di-tert-butyl ester

There total 3 articles about N-<4-(N-Cbz-D,L-erythro,threo-5-oxo-4-oxazolidinyl)-2-fluoropropionyl>-L-glutamic 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: 50.0%

di-tert-butyl L-glutamate (16874-06-9) + 4-(N-Cbz-D,L-erythro,threo-5-oxo-4-oxazolidinyl)-2-fluoropropionic acid (124688-44-4,124688-45-5) → N-<4-(N-Cbz-D,L-erythro,threo-5-oxo-4-oxazolidinyl)-2-fluoropropionyl>-L-glutamic acid di-tert-butyl ester (124688-46-6,124815-52-7,124815-53-8,124815-54-9)

Guidance literature:

With benzotriazol-1-ol; 2`,3`-dideoxycytidine; In dichloromethane; for 72h; Ambient temperature;

DOI:10.1021/jm00165a021

Reference yield:

D,L-erythro,threo-4-fluoroglutamic acid (2708-77-2,149117-03-3,91383-48-1,91383-47-0) → N-<4-(N-Cbz-D,L-erythro,threo-5-oxo-4-oxazolidinyl)-2-fluoropropionyl>-L-glutamic acid di-tert-butyl ester (124688-46-6,124815-52-7,124815-53-8,124815-54-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / NaHCO₃ / H₂O / 5 h

2: 65 percent / TsOH / benzene / 7 h / Heating

3: 50 percent / DDC, HOBt / CH₂Cl₂ / 72 h / Ambient temperature

With sodium hydrogencarbonate; benzotriazol-1-ol; toluene-4-sulfonic acid; 2`,3`-dideoxycytidine; In dichloromethane; water; benzene;

DOI:10.1021/jm00165a021

Reference yield:

N-benzyloxycarbonyl-4-(R/S)-fluoro-D/L-glutamic acid (124688-42-2,124688-43-3) → N-<4-(N-Cbz-D,L-erythro,threo-5-oxo-4-oxazolidinyl)-2-fluoropropionyl>-L-glutamic acid di-tert-butyl ester (124688-46-6,124815-52-7,124815-53-8,124815-54-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / TsOH / benzene / 7 h / Heating

2: 50 percent / DDC, HOBt / CH₂Cl₂ / 72 h / Ambient temperature

With benzotriazol-1-ol; toluene-4-sulfonic acid; 2`,3`-dideoxycytidine; In dichloromethane; benzene;

DOI:10.1021/jm00165a021

upstream raw materials:

di-tert-butyl L-glutamate

4-(N-Cbz-D,L-erythro,threo-5-oxo-4-oxazolidinyl)-2-fluoropropionic acid

D,L-erythro,threo-4-fluoroglutamic acid

N-benzyloxycarbonyl-4-(R/S)-fluoro-D/L-glutamic acid

Refernces