N-[(2SR,5S)-2-[N-benzyloxycarbonylamino-L-threonylaminomethyl]-5-[N-(tert-butoxycarbonyl)amino]-4-oxo-7-methyloctanoyl]-L-leucinamide

Base Information

Chemical Name:N-[(2SR,5S)-2-[N-benzyloxycarbonylamino-L-threonylaminomethyl]-5-[N-(tert-butoxycarbonyl)amino]-4-oxo-7-methyloctanoyl]-L-leucinamide
CAS No.:628318-90-1
Molecular Formula:C₃₃H₅₃N₅O₉
Molecular Weight:663.812
Hs Code.:

Synonyms:N-[(2SR,5S)-2-[N-benzyloxycarbonylamino-L-threonylaminomethyl]-5-[N-(tert-butoxycarbonyl)amino]-4-oxo-7-methyloctanoyl]-L-leucinamide

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Chemical Property of N-[(2SR,5S)-2-[N-benzyloxycarbonylamino-L-threonylaminomethyl]-5-[N-(tert-butoxycarbonyl)amino]-4-oxo-7-methyloctanoyl]-L-leucinamide

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Technology Process of N-[(2SR,5S)-2-[N-benzyloxycarbonylamino-L-threonylaminomethyl]-5-[N-(tert-butoxycarbonyl)amino]-4-oxo-7-methyloctanoyl]-L-leucinamide

There total 8 articles about N-[(2SR,5S)-2-[N-benzyloxycarbonylamino-L-threonylaminomethyl]-5-[N-(tert-butoxycarbonyl)amino]-4-oxo-7-methyloctanoyl]-L-leucinamide 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%

: 628318-89-8
N-[(2SR,5S)-2-[N-benzyloxycarbonylamino-O-(tert-butyldimethylsiloxy)-L-threonylaminomethyl]-5-[N-(tert-butoxycarbonyl)amino]-4-oxo-7-methyloctanoyl]-L-leucinamide

: 628318-90-1
N-[(2SR,5S)-2-[N-benzyloxycarbonylamino-L-threonylaminomethyl]-5-[N-(tert-butoxycarbonyl)amino]-4-oxo-7-methyloctanoyl]-L-leucinamide

Guidance literature:: With acetic acid; In water; at 25 ℃; for 96h;
DOI:10.1021/jo034837z

Reference yield:

: 52716-49-1
N-((3S)-1-bromo-2-oxo-5-methyl-3-hexyl)-t-butoxycarboxamide

: 628318-90-1
N-[(2SR,5S)-2-[N-benzyloxycarbonylamino-L-threonylaminomethyl]-5-[N-(tert-butoxycarbonyl)amino]-4-oxo-7-methyloctanoyl]-L-leucinamide

Guidance literature:: Multi-step reaction with 7 steps

1.1: NaH / tetrahydrofuran / 0.25 h / 0 °C

1.2: 70 percent / tetrahydrofuran / 1.5 h

2.1: NaBH₄ / methanol; 2-methoxy-ethanol / 0.33 h

2.2: 51 percent / DMAP / CH₂Cl₂ / 24 h

3.1: 89 percent / Sn(OAc)2; (i-Pr)2NEt / dimethylformamide / 17 h / 80 °C

4.1: H₂; AcOH / PtO₂ / 5 h / 20 °C

5.1: 59 percent / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide / dimethylformamide / 3 h

6.1: 96 percent / sulfur trioxide pyridine complex; triethylamine / dimethylsulfoxide / 48 h

7.1: 82 percent / AcOH / H₂O / 96 h / 25 °C

With sodium tetrahydroborate; hydrogen; tin(II) acetate; sulfur trioxide pyridine complex; sodium hydride; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; platinum(IV) oxide; In tetrahydrofuran; methanol; 2-methoxy-ethanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jo034837z

Reference yield:

: 630046-94-5
methyl (2SR,5S)-5-[N-(tert-butoxycarbonyl)amino]-2-cyano-7-methyl-4-oxooctanoate

: 628318-90-1
N-[(2SR,5S)-2-[N-benzyloxycarbonylamino-L-threonylaminomethyl]-5-[N-(tert-butoxycarbonyl)amino]-4-oxo-7-methyloctanoyl]-L-leucinamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaBH₄ / methanol; 2-methoxy-ethanol / 0.33 h

1.2: 51 percent / DMAP / CH₂Cl₂ / 24 h

2.1: 89 percent / Sn(OAc)2; (i-Pr)2NEt / dimethylformamide / 17 h / 80 °C

3.1: H₂; AcOH / PtO₂ / 5 h / 20 °C

4.1: 59 percent / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide / dimethylformamide / 3 h

5.1: 96 percent / sulfur trioxide pyridine complex; triethylamine / dimethylsulfoxide / 48 h

6.1: 82 percent / AcOH / H₂O / 96 h / 25 °C

With sodium tetrahydroborate; hydrogen; tin(II) acetate; sulfur trioxide pyridine complex; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; platinum(IV) oxide; In methanol; 2-methoxy-ethanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jo034837z