benzyl N-{2-[N-(2-tert-butoxycarbonylaminoethyl)-N-(prop-2-en-1-yloxycarbonyl)]glycylaminoethyl}-N-[(9H-fluoren-9-yl)methyloxycarbonyl]glycinate

Base Information

• Chemical Name: benzyl N-{2-[N-(2-tert-butoxycarbonylaminoethyl)-N-(prop-2-en-1-yloxycarbonyl)]glycylaminoethyl}-N-[(9H-fluoren-9-yl)methyloxycarbonyl]glycinate
• CAS No.: 1352089-50-9
• Molecular Formula: C₃₉H₄₆N₄O₉
• Molecular Weight: 714.816
• Mol file: 1352089-50-9.mol

Synonyms:benzyl N-{2-[N-(2-tert-butoxycarbonylaminoethyl)-N-(prop-2-en-1-yloxycarbonyl)]glycylaminoethyl}-N-[(9H-fluoren-9-yl)methyloxycarbonyl]glycinate

Chemical Property of benzyl N-{2-[N-(2-tert-butoxycarbonylaminoethyl)-N-(prop-2-en-1-yloxycarbonyl)]glycylaminoethyl}-N-[(9H-fluoren-9-yl)methyloxycarbonyl]glycinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl N-{2-[N-(2-tert-butoxycarbonylaminoethyl)-N-(prop-2-en-1-yloxycarbonyl)]glycylaminoethyl}-N-[(9H-fluoren-9-yl)methyloxycarbonyl]glycinate

There total 6 articles about benzyl N-{2-[N-(2-tert-butoxycarbonylaminoethyl)-N-(prop-2-en-1-yloxycarbonyl)]glycylaminoethyl}-N-[(9H-fluoren-9-yl)methyloxycarbonyl]glycinate 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: 73.0%

H-Aeg(Fmoc)-OBn*TFA (1421940-85-3) + N-<2-(N-Boc)aminoethyl>-N-glycine (221554-92-3) → benzyl N-{2-[N-(2-tert-butoxycarbonylaminoethyl)-N-(prop-2-en-1-yloxycarbonyl)]glycylaminoethyl}-N-[(9H-fluoren-9-yl)methyloxycarbonyl]glycinate (1352089-50-9)

Guidance literature:

N-<2-(N-Boc)aminoethyl>-N-glycine; With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 0.5h; Inert atmosphere;

H-Aeg(Fmoc)-OBn*TFA; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;

DOI:10.1002/hlca.201100243

Reference yield:

benzyl N-(2-aminoethyl)glycinate ditosylate → benzyl N-{2-[N-(2-tert-butoxycarbonylaminoethyl)-N-(prop-2-en-1-yloxycarbonyl)]glycylaminoethyl}-N-[(9H-fluoren-9-yl)methyloxycarbonyl]glycinate (1352089-50-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 5.33 h / 0 - 20 °C / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

3.1: triethylsilane / dichloromethane / 3 h / 0 - 20 °C

4.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h / Inert atmosphere

4.2: 20 °C / Inert atmosphere

With triethylsilane; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/hlca.201100243

Reference yield:

benzyl N-[(9-H-fluoren-9-yl)methoxycarbonyl]-N-(2-tert-butoxycarbonylaminoethyl)glycinate (1352089-48-5) → benzyl N-{2-[N-(2-tert-butoxycarbonylaminoethyl)-N-(prop-2-en-1-yloxycarbonyl)]glycylaminoethyl}-N-[(9H-fluoren-9-yl)methyloxycarbonyl]glycinate (1352089-50-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylsilane / dichloromethane / 3 h / 0 - 20 °C

2.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h / Inert atmosphere

2.2: 20 °C / Inert atmosphere

With triethylsilane; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/hlca.201100243

upstream raw materials:

benzyl N-[(9-H-fluoren-9-yl)methoxycarbonyl]-N-(2-tert-butoxycarbonylaminoethyl)glycinate

H-Aeg(Fmoc)-OBn*TFA

N-<2-(N-Boc)aminoethyl>-N-glycine

methyl N-(2-(tert-butyloxycarbonyl)aminoethyl)glycinate

Downstream raw materials:

benzyl N-(2-(N-(allyloxycarbonyl)-N-(2-(N-(2-(4-(benzyloxycarbonylamino)-2-oxopyrimidin-1-yl)acetyl)-N-(2-(tert-butoxycarbonylamino)ethyl)glycylamino)ethyl)glycylamino)ethyl)-N-((9H-fluoren-9-yl)methyloxycarbonyl)glycinate

benzyl N-(2-(N-(allyloxycarbonyl)-N-(2-(N-(2-(4-(benzyloxycarbonylamino)-2-oxopyrimidin-1-yl)acetyl)-N-(2-(tert-butoxycarbonylamino)ethyl)glycylamino)ethyl)glycylamino)ethyl)glycinate

Boc-Aeg(C[z])-Aeg(Alloc)-Aeg(G[z])-OBn

Boc-Aeg(C[z])-Aeg(H)-Aeg(G[z])-OBn