benzyl (2S,3S,4R)-4-<(N^α,N^im-bis(tert-butoxycarbonyl)-(S)-erythro-β-hydroxyhistidyl)amino>-3-hydroxy-2-methylvalerate

Base Information

• Chemical Name: benzyl (2S,3S,4R)-4-<(N^α,N^im-bis(tert-butoxycarbonyl)-(S)-erythro-β-hydroxyhistidyl)amino>-3-hydroxy-2-methylvalerate
• CAS No.: 82691-98-3
• Molecular Formula: C₂₉H₄₂N₄O₉
• Molecular Weight: 590.674

Synonyms:benzyl (2S,3S,4R)-4-<(N^α,N^im-bis(tert-butoxycarbonyl)-(S)-erythro-β-hydroxyhistidyl)amino>-3-hydroxy-2-methylvalerate

Chemical Property of benzyl (2S,3S,4R)-4-<(N^α,N^im-bis(tert-butoxycarbonyl)-(S)-erythro-β-hydroxyhistidyl)amino>-3-hydroxy-2-methylvalerate

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Technology Process of benzyl (2S,3S,4R)-4-<(N^α,N^im-bis(tert-butoxycarbonyl)-(S)-erythro-β-hydroxyhistidyl)amino>-3-hydroxy-2-methylvalerate

There total 8 articles about benzyl (2S,3S,4R)-4-<(N^α,N^im-bis(tert-butoxycarbonyl)-(S)-erythro-β-hydroxyhistidyl)amino>-3-hydroxy-2-methylvalerate 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: 62.0%

Nα,Nim-bis(tert-butoxycarbonyl)-erythro-β-hydroxy-L-histidine (82692-03-3) + benzyl (2S,3S,4R)-4-amino-3-hydroxy-2-methylvalerate (82692-04-4) → benzyl (2S,3S,4R)-4-<(Nα,Nim-bis(tert-butoxycarbonyl)-(S)-erythro-β-hydroxyhistidyl)amino>-3-hydroxy-2-methylvalerate (82691-98-3)

Guidance literature:

With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 25 ℃; for 16h;

DOI:10.1021/ja00383a045

Reference yield: 32.0%

Nα,Nim-bis(tert-butoxycarbonyl)-erythro-β-hydroxy-L-histidine (82692-03-3) + benzyl (2S,3S,4R)-4-amino-3-hydroxy-2-methylvalerate hydrochloride → benzyl (2S,3S,4R)-4-<(Nα,Nim-bis(tert-butoxycarbonyl)-(S)-erythro-β-hydroxyhistidyl)amino>-3-hydroxy-2-methylvalerate (82691-98-3)

Guidance literature:

With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In dichloromethane; 1.) 0 deg C, 1 h, 2.) 25 deg C, 24 h;

DOI:10.1021/ja00042a002

Reference yield:

(2S,3S,4R)-4-amino-3-hydroxy-2-methylpentanoic acid (18710-32-2) → benzyl (2S,3S,4R)-4-<(Nα,Nim-bis(tert-butoxycarbonyl)-(S)-erythro-β-hydroxyhistidyl)amino>-3-hydroxy-2-methylvalerate (82691-98-3)

Guidance literature:

Multi-step reaction with 2 steps

1: HCl / 12 h / 25 °C

2: 62 percent / DCC, HOBt / dimethylformamide / 16 h / 25 °C

With hydrogenchloride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide;

DOI:10.1021/ja00383a045

upstream raw materials:

N^α,N^im-bis(tert-butoxycarbonyl)-erythro-β-hydroxy-L-histidine

benzyl (2S,3S,4R)-4-amino-3-hydroxy-2-methylvalerate

N-(tert-butyloxycarbonyl) azide

(2S,3S,4R)-4-amino-3-hydroxy-2-methylpentanoic acid

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