benzyl N-{trans-(2S)-2-[2-(tert-butoxycarbonylamino)cyclopropyloxy]propionyl}-L-alanyl-D-isoglutaminate

Base Information

• Chemical Name: benzyl N-{trans-(2S)-2-[2-(tert-butoxycarbonylamino)cyclopropyloxy]propionyl}-L-alanyl-D-isoglutaminate
• CAS No.: 682747-33-7
• Molecular Formula: C₂₆H₃₈N₄O₈
• Molecular Weight: 534.61
• Mol file: 682747-33-7.mol

Synonyms:benzyl N-{trans-(2S)-2-[2-(tert-butoxycarbonylamino)cyclopropyloxy]propionyl}-L-alanyl-D-isoglutaminate

Chemical Property of benzyl N-{trans-(2S)-2-[2-(tert-butoxycarbonylamino)cyclopropyloxy]propionyl}-L-alanyl-D-isoglutaminate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl N-{trans-(2S)-2-[2-(tert-butoxycarbonylamino)cyclopropyloxy]propionyl}-L-alanyl-D-isoglutaminate

There total 8 articles about benzyl N-{trans-(2S)-2-[2-(tert-butoxycarbonylamino)cyclopropyloxy]propionyl}-L-alanyl-D-isoglutaminate 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%

L-alanyl-D-isoglutamine benzyl ester hydrochloride (59524-62-8) + trans-(2S)-2-(2-[(tert-butoxycarbonyl)amino]cyclopropyloxy)propanoic acid (682747-32-6) → benzyl N-{trans-(2S)-2-[2-(tert-butoxycarbonylamino)cyclopropyloxy]propionyl}-L-alanyl-D-isoglutaminate (682747-33-7)

Guidance literature:

trans-(2S)-2-(2-[(tert-butoxycarbonyl)amino]cyclopropyloxy)propanoic acid; With 4-methyl-morpholine; isobutyl chloroformate; In ethyl acetate; N,N-dimethyl-formamide; at -15 ℃; for 0.0833333h;

L-alanyl-D-isoglutamine benzyl ester hydrochloride; With 4-methyl-morpholine; In ethyl acetate; N,N-dimethyl-formamide; for 18h; Further stages.;

DOI:10.1016/j.tet.2004.01.037

Reference yield: 45.0%

L-alanyl-D-isoglutamine benzyl ester hydrochloride (59524-62-8) + cis-(2S)-2-(2-[(tert-butoxycarbonyl)amino]cyclopropyloxy)propanoic acid (682747-32-6) → benzyl N-{cis-(2S)-2-[2-(tert-butoxycarbonylamino)cyclopropyloxy]propionyl}-L-alanyl-D-isoglutaminate (682747-33-7)

Guidance literature:

cis-(2S)-2-(2-[(tert-butoxycarbonyl)amino]cyclopropyloxy)propanoic acid; With 4-methyl-morpholine; isobutyl chloroformate; In ethyl acetate; N,N-dimethyl-formamide; at -15 ℃; for 0.0833333h;

L-alanyl-D-isoglutamine benzyl ester hydrochloride; With 4-methyl-morpholine; In ethyl acetate; N,N-dimethyl-formamide; for 18h; Further stages.;

DOI:10.1016/j.tet.2004.01.037

Reference yield:

isopropyl (2S)-2-(vinyloxy)propanoate (682747-28-0) → benzyl N-{trans-(2S)-2-[2-(tert-butoxycarbonylamino)cyclopropyloxy]propionyl}-L-alanyl-D-isoglutaminate (682747-33-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 28 percent / [(Rh(OAc)2)2] / CH₂Cl₂ / 8 h / 25 °C

2.1: CF₃COOH / CH₂Cl₂ / 18 h

3.1: 14 percent / DPPA; triethylamine / 3 h / 80 °C

4.1: KOH; ethanol / 3 h / 25 °C

5.1: isobutyl chloroformate; N-methyl-morpholine / ethyl acetate; dimethylformamide / 0.08 h / -15 °C

5.2: 90 percent / N-methyl-morpholine / ethyl acetate; dimethylformamide / 18 h

With 4-methyl-morpholine; dirhodium tetraacetate; potassium hydroxide; ethanol; diphenyl-phosphinic acid; triethylamine; trifluoroacetic acid; isobutyl chloroformate; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2004.01.037

upstream raw materials:

L-alanyl-D-isoglutamine benzyl ester hydrochloride

cis-(2S)-2-(2-[(tert-butoxycarbonyl)amino]cyclopropyloxy)propanoic acid

isopropyl cis-(2S)-2-[2-(tert-butoxycarbonyl)cyclopropyl]oxy-propanoate

isopropyl cis-(2S)-2-(2-[(tert-butoxycarbonyl)amino]cyclopropyloxy)propanoate

Downstream raw materials:

benzyl N-{cis-(2S)-2-[2-(acetylamino)cyclopropyloxy]-propionyl}-L-alanyl-D-isoglutaminate

benzyl {cis-(2S)-2-[2-(octanoylamino)cyclopropyloxy]propionyl}-L-alanyl-D-isoglutaminate

benzyl N-{trans-(2S)-2-[2-(acetylamino)cyclopropyloxy]-propionyl}-L-alanyl-D-isoglutaminate

benzyl {trans-(2S)-2-[2-(octanoylamino)cyclopropyloxy]propionyl}-L-alanyl-D-isoglutaminate