O-benzyl 4(S)-<(tert-butyloxycarbonyl)amino>-2,2-difluoro-3(R)-hydroxy-6-methylheptanohydroxamate

Base Information

• Chemical Name: O-benzyl 4(S)-<(tert-butyloxycarbonyl)amino>-2,2-difluoro-3(R)-hydroxy-6-methylheptanohydroxamate
• CAS No.: 109553-23-3
• Molecular Formula: C₂₀H₃₀F₂N₂O₅
• Molecular Weight: 416.465
• Mol file: 109553-23-3.mol

Synonyms:O-benzyl 4(S)-<(tert-butyloxycarbonyl)amino>-2,2-difluoro-3(R)-hydroxy-6-methylheptanohydroxamate

Chemical Property of O-benzyl 4(S)-<(tert-butyloxycarbonyl)amino>-2,2-difluoro-3(R)-hydroxy-6-methylheptanohydroxamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of O-benzyl 4(S)-<(tert-butyloxycarbonyl)amino>-2,2-difluoro-3(R)-hydroxy-6-methylheptanohydroxamate

There total 1 articles about O-benzyl 4(S)-<(tert-butyloxycarbonyl)amino>-2,2-difluoro-3(R)-hydroxy-6-methylheptanohydroxamate 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%

O-benzylhydoxylamine hydrochloride (2687-43-6) + sodium 4(S)-<(tert-butyloxycarbonyl)amino>-2,2-difluoro-3(R)-hydroxy-6-methylheptanoate (103322-63-0) → O-benzyl 4(S)-<(tert-butyloxycarbonyl)amino>-2,2-difluoro-3(R)-hydroxy-6-methylheptanohydroxamate (109553-23-3)

Guidance literature:

With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In dichloromethane; for 24h; Ambient temperature;

DOI:10.1021/jm00393a026

Reference yield: 54.0%

O-benzyl 4(S)-<(tert-butyloxycarbonyl)amino>-2,2-difluoro-3(R)-hydroxy-6-methylheptanohydroxamate (109553-23-3) → 1-(benzyloxy)-4(S)-<1(S)-<(tert-butoxycarbonyl)amino>-3-methylbutyl>-3,3-difluoro-2-azetidinone (109553-24-4)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 50 ℃; for 0.75h;

DOI:10.1021/jm00393a026

Reference yield:

O-benzyl 4(S)-<(tert-butyloxycarbonyl)amino>-2,2-difluoro-3(R)-hydroxy-6-methylheptanohydroxamate (109553-23-3) → sodium 3(S)-<(benzyloxy)amino>-4(S)-<(tert-butyloxycarbonyl)amino>-2,2-difluoro-6-methylheptanoate (109553-25-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 54 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 0.75 h / 50 °C

2: 1M aq. NaOH / tetrahydrofuran / 20 h

With sodium hydroxide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran;

DOI:10.1021/jm00393a026

upstream raw materials:

O-benzylhydoxylamine hydrochloride

sodium 4(S)-<(tert-butyloxycarbonyl)amino>-2,2-difluoro-3(R)-hydroxy-6-methylheptanoate

Downstream raw materials:

1-(benzyloxy)-4(S)-<1(S)-<(tert-butoxycarbonyl)amino>-3-methylbutyl>-3,3-difluoro-2-azetidinone

sodium 3(S)-<(benzyloxy)amino>-4(S)-<(tert-butyloxycarbonyl)amino>-2,2-difluoro-6-methylheptanoate

Refernces