(2S,5S,6S)-3-aza-3-(benzyloxycarbonyl)-6-[(tert-butyloxycarbonyl)amino]-5-hydroxy-2-methyl-7-phenylheptanoyl amide

Base Information

• Chemical Name: (2S,5S,6S)-3-aza-3-(benzyloxycarbonyl)-6-[(tert-butyloxycarbonyl)amino]-5-hydroxy-2-methyl-7-phenylheptanoyl amide
• CAS No.: 500767-19-1
• Molecular Formula: C₂₆H₃₅N₃O₆
• Molecular Weight: 485.58

Synonyms:(2S,5S,6S)-3-aza-3-(benzyloxycarbonyl)-6-[(tert-butyloxycarbonyl)amino]-5-hydroxy-2-methyl-7-phenylheptanoyl amide

Chemical Property of (2S,5S,6S)-3-aza-3-(benzyloxycarbonyl)-6-[(tert-butyloxycarbonyl)amino]-5-hydroxy-2-methyl-7-phenylheptanoyl amide

Chemical Property:

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Technology Process of (2S,5S,6S)-3-aza-3-(benzyloxycarbonyl)-6-[(tert-butyloxycarbonyl)amino]-5-hydroxy-2-methyl-7-phenylheptanoyl amide

There total 2 articles about (2S,5S,6S)-3-aza-3-(benzyloxycarbonyl)-6-[(tert-butyloxycarbonyl)amino]-5-hydroxy-2-methyl-7-phenylheptanoyl amide 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: 98.0%

benzyl chloroformate (501-53-1,94274-21-2) + (2S,5S,6S)-3-aza-6-[(tert-butyloxycarbonyl)amino]-5-hydroxy-2-methyl-7-phenylheptanoyl amide (500767-12-4) → (2S,5S,6S)-3-aza-3-(benzyloxycarbonyl)-6-[(tert-butyloxycarbonyl)amino]-5-hydroxy-2-methyl-7-phenylheptanoyl amide (500767-19-1)

Guidance literature:

With sodium carbonate; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1021/jm020951i

Reference yield:

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8) → (2S,5S,6S)-3-aza-3-(benzyloxycarbonyl)-6-[(tert-butyloxycarbonyl)amino]-5-hydroxy-2-methyl-7-phenylheptanoyl amide (500767-19-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / propan-2-ol / Heating

2: 98 percent / aq. Na₂CO₃ / tetrahydrofuran / 0.5 h / 20 °C

With sodium carbonate; In tetrahydrofuran; isopropyl alcohol;

DOI:10.1021/jm020951i

Reference yield:

(2S,5S,6S)-3-aza-3-(benzyloxycarbonyl)-6-[(tert-butyloxycarbonyl)amino]-5-hydroxy-2-methyl-7-phenylheptanoyl amide (500767-19-1) → ((2S,3S)-3-Amino-2-hydroxy-4-phenyl-butyl)-((S)-1-carbamoyl-ethyl)-carbamic acid benzyl ester

Guidance literature:

With hydrogenchloride; In ethyl acetate; at 20 ℃; for 0.25h;

DOI:10.1021/jm020951i

upstream raw materials:

benzyl chloroformate

(2S,5S,6S)-3-aza-6-[(tert-butyloxycarbonyl)amino]-5-hydroxy-2-methyl-7-phenylheptanoyl amide

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

Downstream raw materials:

(2S,5S,6S)-3-aza-3-(benzyloxycarbonyl)-6-[[(tert-butyloxycarbonyl)-L-valinyl]amino]-5-hydroxy-2-methyl-7-phenylheptanoyl amide

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