(3'S,5RS)-5-[N-[3-benzyloxycarbonylamino-6-[2,3-di(benzyloxycarbonyl)-1-methylguanidin-1-yl]hexanoyl]-N-methylamino]-5,6-dihydro-2-ureidopyrimid-4(1H)-one

Base Information

• Chemical Name: (3'S,5RS)-5-[N-[3-benzyloxycarbonylamino-6-[2,3-di(benzyloxycarbonyl)-1-methylguanidin-1-yl]hexanoyl]-N-methylamino]-5,6-dihydro-2-ureidopyrimid-4(1H)-one
• CAS No.: 468071-53-6
• Molecular Formula: C₃₈H₄₅N₉O₉
• Molecular Weight: 771.83

Synonyms:(3'S,5RS)-5-[N-[3-benzyloxycarbonylamino-6-[2,3-di(benzyloxycarbonyl)-1-methylguanidin-1-yl]hexanoyl]-N-methylamino]-5,6-dihydro-2-ureidopyrimid-4(1H)-one

Chemical Property of (3'S,5RS)-5-[N-[3-benzyloxycarbonylamino-6-[2,3-di(benzyloxycarbonyl)-1-methylguanidin-1-yl]hexanoyl]-N-methylamino]-5,6-dihydro-2-ureidopyrimid-4(1H)-one

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Technology Process of (3'S,5RS)-5-[N-[3-benzyloxycarbonylamino-6-[2,3-di(benzyloxycarbonyl)-1-methylguanidin-1-yl]hexanoyl]-N-methylamino]-5,6-dihydro-2-ureidopyrimid-4(1H)-one

There total 4 articles about (3'S,5RS)-5-[N-[3-benzyloxycarbonylamino-6-[2,3-di(benzyloxycarbonyl)-1-methylguanidin-1-yl]hexanoyl]-N-methylamino]-5,6-dihydro-2-ureidopyrimid-4(1H)-one 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%

rac-1,4,5,6-tetrahydro-5-methylamino-2-ureidopyrimidin-4-one (207570-27-2) + Nβ,Nω,Nω'-tris(benzyloxycarbonyl)-Nε-methyl-(S)-β-homoarginine (468071-25-2) → (3'S,5RS)-5-[N-[3-benzyloxycarbonylamino-6-[2,3-di(benzyloxycarbonyl)-1-methylguanidin-1-yl]hexanoyl]-N-methylamino]-5,6-dihydro-2-ureidopyrimid-4(1H)-one (468071-53-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/jm0111191

Reference yield:

N,N-bis(benzyloxycarbonyl)-1H-pyrazole-1-carboxamidine (152120-55-3) → (3'S,5RS)-5-[N-[3-benzyloxycarbonylamino-6-[2,3-di(benzyloxycarbonyl)-1-methylguanidin-1-yl]hexanoyl]-N-methylamino]-5,6-dihydro-2-ureidopyrimid-4(1H)-one (468071-53-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / Et₃N / CH₂Cl₂ / Heating

2: 59 percent / Et₃SiH; TFA / CH₂Cl₂ / -5 °C

3: 82 percent / HATU; DIPEA / dimethylformamide / 20 °C

With triethylsilane; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm0111191

Reference yield:

Nβ-benzyloxycarbonyl-Nε-methyl-(S)-β-lysine tert-butyl ester hydrochloride → (3'S,5RS)-5-[N-[3-benzyloxycarbonylamino-6-[2,3-di(benzyloxycarbonyl)-1-methylguanidin-1-yl]hexanoyl]-N-methylamino]-5,6-dihydro-2-ureidopyrimid-4(1H)-one (468071-53-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / Et₃N / CH₂Cl₂ / Heating

2: 59 percent / Et₃SiH; TFA / CH₂Cl₂ / -5 °C

3: 82 percent / HATU; DIPEA / dimethylformamide / 20 °C

With triethylsilane; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm0111191

upstream raw materials:

rac-1,4,5,6-tetrahydro-5-methylamino-2-ureidopyrimidin-4-one

N^β,N^ω,N^ω'-tris(benzyloxycarbonyl)-N^ε-methyl-(S)-β-homoarginine

N,N-bis(benzyloxycarbonyl)-1H-pyrazole-1-carboxamidine

N^β,N^ω,N^ω'-tris(benzyloxycarbonyl)-N^ε-methyl-(S)-β-homoarginine tert-butyl ester

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