((R)-5-{[((S)-1-{Amino-[(E)-benzyloxycarbonylimino]-methyl}-2-oxo-piperidin-3-ylcarbamoyl)-methyl]-carbamoyl}-5-tert-butoxycarbonylamino-pentyl)-carbamic acid benzyl ester

Base Information

• Chemical Name: ((R)-5-{[((S)-1-{Amino-[(E)-benzyloxycarbonylimino]-methyl}-2-oxo-piperidin-3-ylcarbamoyl)-methyl]-carbamoyl}-5-tert-butoxycarbonylamino-pentyl)-carbamic acid benzyl ester
• CAS No.: 186368-97-8
• Molecular Formula: C₃₅H₄₇N₇O₉
• Molecular Weight: 709.8

Synonyms:

Chemical Property of ((R)-5-{[((S)-1-{Amino-[(E)-benzyloxycarbonylimino]-methyl}-2-oxo-piperidin-3-ylcarbamoyl)-methyl]-carbamoyl}-5-tert-butoxycarbonylamino-pentyl)-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of ((R)-5-{[((S)-1-{Amino-[(E)-benzyloxycarbonylimino]-methyl}-2-oxo-piperidin-3-ylcarbamoyl)-methyl]-carbamoyl}-5-tert-butoxycarbonylamino-pentyl)-carbamic acid benzyl ester

There total 5 articles about ((R)-5-{[((S)-1-{Amino-[(E)-benzyloxycarbonylimino]-methyl}-2-oxo-piperidin-3-ylcarbamoyl)-methyl]-carbamoyl}-5-tert-butoxycarbonylamino-pentyl)-carbamic acid benzyl 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:

t-butyloxycarbonyl-L-arginine (13726-76-6,78603-12-0) → ((R)-5-{[((S)-1-{Amino-[(E)-benzyloxycarbonylimino]-methyl}-2-oxo-piperidin-3-ylcarbamoyl)-methyl]-carbamoyl}-5-tert-butoxycarbonylamino-pentyl)-carbamic acid benzyl ester (186368-97-8)

Guidance literature:

Multi-step reaction with 4 steps

1: aq. NaHCO₃

2: iBuO₂CCl; NMM

3: HCl / dioxane

4: BOP; DIEA / dimethylformamide

With 4-methyl-morpholine; hydrogenchloride; sodium hydrogencarbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; isobutyl chloroformate; In 1,4-dioxane; N,N-dimethyl-formamide; 1: Acylation / 2: Cyclization / 3: Acidolysis / 4: Condensation;

DOI:10.1016/S0960-894X(99)00582-X

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → ((R)-5-{[((S)-1-{Amino-[(E)-benzyloxycarbonylimino]-methyl}-2-oxo-piperidin-3-ylcarbamoyl)-methyl]-carbamoyl}-5-tert-butoxycarbonylamino-pentyl)-carbamic acid benzyl ester (186368-97-8)

Guidance literature:

Multi-step reaction with 4 steps

1: aq. NaHCO₃

2: iBuO₂CCl; NMM

3: HCl / dioxane

4: BOP; DIEA / dimethylformamide

With 4-methyl-morpholine; hydrogenchloride; sodium hydrogencarbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; isobutyl chloroformate; In 1,4-dioxane; N,N-dimethyl-formamide; 1: Acylation / 2: Cyclization / 3: Acidolysis / 4: Condensation;

DOI:10.1016/S0960-894X(99)00582-X

Reference yield:

((S)-1-{Amino-[(E)-benzyloxycarbonylimino]-methyl}-2-oxo-piperidin-3-yl)-carbamic acid tert-butyl ester (51219-20-6) → ((R)-5-{[((S)-1-{Amino-[(E)-benzyloxycarbonylimino]-methyl}-2-oxo-piperidin-3-ylcarbamoyl)-methyl]-carbamoyl}-5-tert-butoxycarbonylamino-pentyl)-carbamic acid benzyl ester (186368-97-8)

Guidance literature:

Multi-step reaction with 2 steps

1: HCl / dioxane

2: BOP; DIEA / dimethylformamide

With hydrogenchloride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; N,N-dimethyl-formamide; 1: Acidolysis / 2: Condensation;

DOI:10.1016/S0960-894X(99)00582-X

upstream raw materials:

[1-Amino-1-((S)-3-amino-2-oxo-piperidin-1-yl)-meth-(E)-ylidene]-carbamic acid benzyl ester

t-butyloxycarbonyl-L-arginine

benzyl chloroformate

((S)-1-{Amino-[(E)-benzyloxycarbonylimino]-methyl}-2-oxo-piperidin-3-yl)-carbamic acid tert-butyl ester

Downstream raw materials:

C₃₅H₄₉N₇O₉

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