N-triphenylmethyl-(3S)-3-[(2S,3S,4S)-3-azido-2-hydroxy-4-methylhexylamino]-4-(tert-butyldiphenylsilyloxy)butyramide

Base Information

• Chemical Name: N-triphenylmethyl-(3S)-3-[(2S,3S,4S)-3-azido-2-hydroxy-4-methylhexylamino]-4-(tert-butyldiphenylsilyloxy)butyramide
• CAS No.: 439688-96-7
• Molecular Formula: C₄₆H₅₅N₅O₃Si
• Molecular Weight: 754.06

Synonyms:N-triphenylmethyl-(3S)-3-[(2S,3S,4S)-3-azido-2-hydroxy-4-methylhexylamino]-4-(tert-butyldiphenylsilyloxy)butyramide

Chemical Property of N-triphenylmethyl-(3S)-3-[(2S,3S,4S)-3-azido-2-hydroxy-4-methylhexylamino]-4-(tert-butyldiphenylsilyloxy)butyramide

Chemical Property:

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Technology Process of N-triphenylmethyl-(3S)-3-[(2S,3S,4S)-3-azido-2-hydroxy-4-methylhexylamino]-4-(tert-butyldiphenylsilyloxy)butyramide

There total 2 articles about N-triphenylmethyl-(3S)-3-[(2S,3S,4S)-3-azido-2-hydroxy-4-methylhexylamino]-4-(tert-butyldiphenylsilyloxy)butyramide 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: 68.0%

N-Triphenylmethyl (3S)-3-amino-4-(tert-butyldiphenylsilyloxy)butyramide (245523-23-3) + (4S)-3-azido-1,2-epoxy-4-methylhexane → N-triphenylmethyl-(3S)-3-[(2S,3S,4S)-3-azido-2-hydroxy-4-methylhexylamino]-4-(tert-butyldiphenylsilyloxy)butyramide (439688-96-7)

Guidance literature:

In ethanol; for 96h; Heating;

DOI:10.1021/jm0110744

Reference yield:

Benzoic acid (S)-3-azido-2-hydroxy-4-methyl-hexyl ester → N-triphenylmethyl-(3S)-3-[(2S,3S,4S)-3-azido-2-hydroxy-4-methylhexylamino]-4-(tert-butyldiphenylsilyloxy)butyramide (439688-96-7)

Guidance literature:

Multi-step reaction with 3 steps

1: CH₂Cl₂ / 0 - 20 °C

2: 90 percent / NaOEt / ethanol; tetrahydrofuran / 0.5 h / 20 °C

3: 68 percent / ethanol / 96 h / Heating

With sodium ethanolate; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1021/jm0110744

Reference yield: 86.0%

triethylsilyl chloride (994-30-9) + N-triphenylmethyl-(3S)-3-[(2S,3S,4S)-3-azido-2-hydroxy-4-methylhexylamino]-4-(tert-butyldiphenylsilyloxy)butyramide (439688-96-7) → N-triphenylmethyl-(3S)-3-[(2S,3S,4S)-3-azido-4-methyl-2-triethylsilyloxyhexylamino]-4-(tert-butyldiphenylsilyloxy)butyramide (439688-97-8)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 0 - 20 ℃; for 20h;

DOI:10.1021/jm0110744

upstream raw materials:

N-Triphenylmethyl (3S)-3-amino-4-(tert-butyldiphenylsilyloxy)butyramide

Downstream raw materials:

N-triphenylmethyl-(3S)-3-[(2S,3S,4S)-3-azido-4-methyl-2-triethylsilyloxyhexylamino]-4-(tert-butyldiphenylsilyloxy)butyramide

N-triphenylmethyl-(3S)-3-{(2S,6S)-6-[(1S,2S)-1-azido-2-methylbutyl]-2-isopropylmorpholin-3-one-4-yl}-4-hydroxybutyramide

N-triphenylmethyl-(3S)-{(2S,6S)-6-[(1S,2S)-1-azido-2-methylbutyl]-2-isopropylmorpholin-3-one-4-yl}-4-(tert-butyldiphenylsilyloxy)butyramide

N-triphenylmethyl-(3S)-3-{N'-[(2S,3S,4S)-3-azido-2-hydroxy-4-methylhexyl]-N'-[(1R)-1-bromo-2-methylpropylcarbonyl]amino}-4-(tert-butyldiphenylsilyloxy)butyramide

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