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

Base Information

Chemical Name:N-[(2SR,4RS,5S)-2-[N-benzyloxycarbonylamino-O-(tert-butyldimethylsiloxy)-L-threonylaminomethyl]-5-[N-(tert-butoxycarbonyl)amino]-4-hydroxy-7-methyloctanoyl]-L-leucinamide
CAS No.:628318-88-7
Molecular Formula:C₃₉H₆₉N₅O₉Si
Molecular Weight:780.09
Hs Code.:

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

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

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

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

There total 6 articles about N-[(2SR,4RS,5S)-2-[N-benzyloxycarbonylamino-O-(tert-butyldimethylsiloxy)-L-threonylaminomethyl]-5-[N-(tert-butoxycarbonyl)amino]-4-hydroxy-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: 59.0%

: 94820-26-5
N-benzyloxycarbonyl-O-(tert-butyldimethylsilyl)-L-threonine

: 628318-87-6
N-[(2SR,4RS,5S)-2-aminomethyl-5-[N-(tert-butoxycarbonyl)amino]-4-hydroxy-7-methyloctanoyl]-L-leucinamide

: 628318-88-7
N-[(2SR,4RS,5S)-2-[N-benzyloxycarbonylamino-O-(tert-butyldimethylsiloxy)-L-threonylaminomethyl]-5-[N-(tert-butoxycarbonyl)amino]-4-hydroxy-7-methyloctanoyl]-L-leucinamide

Guidance literature:: With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In N,N-dimethyl-formamide; for 3h;
DOI:10.1021/jo034837z

Reference yield:

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

: 628318-88-7
N-[(2SR,4RS,5S)-2-[N-benzyloxycarbonylamino-O-(tert-butyldimethylsiloxy)-L-threonylaminomethyl]-5-[N-(tert-butoxycarbonyl)amino]-4-hydroxy-7-methyloctanoyl]-L-leucinamide

Guidance literature:: Multi-step reaction with 5 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

With sodium tetrahydroborate; hydrogen; tin(II) acetate; sodium hydride; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; platinum(IV) oxide; In tetrahydrofuran; methanol; 2-methoxy-ethanol; 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

: 628318-88-7
N-[(2SR,4RS,5S)-2-[N-benzyloxycarbonylamino-O-(tert-butyldimethylsiloxy)-L-threonylaminomethyl]-5-[N-(tert-butoxycarbonyl)amino]-4-hydroxy-7-methyloctanoyl]-L-leucinamide

Guidance literature:: Multi-step reaction with 4 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

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