(3S,4S)-3-((1S,2S)-2-Azido-1-hydroxy-butyl)-3-bromo-4-phenyl-1-((S)-1-phenyl-ethyl)-azetidin-2-one

Base Information

• Chemical Name: (3S,4S)-3-((1S,2S)-2-Azido-1-hydroxy-butyl)-3-bromo-4-phenyl-1-((S)-1-phenyl-ethyl)-azetidin-2-one
• CAS No.: 917110-41-9
• Molecular Formula: C₂₁H₂₃BrN₄O₂
• Molecular Weight: 443.343

Synonyms:(3S,4S)-3-((1S,2S)-2-Azido-1-hydroxy-butyl)-3-bromo-4-phenyl-1-((S)-1-phenyl-ethyl)-azetidin-2-one

Chemical Property of (3S,4S)-3-((1S,2S)-2-Azido-1-hydroxy-butyl)-3-bromo-4-phenyl-1-((S)-1-phenyl-ethyl)-azetidin-2-one

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Technology Process of (3S,4S)-3-((1S,2S)-2-Azido-1-hydroxy-butyl)-3-bromo-4-phenyl-1-((S)-1-phenyl-ethyl)-azetidin-2-one

There total 2 articles about (3S,4S)-3-((1S,2S)-2-Azido-1-hydroxy-butyl)-3-bromo-4-phenyl-1-((S)-1-phenyl-ethyl)-azetidin-2-one 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:

(3S,4S)-3-Bromo-3-((2S,3R)-3-ethyl-oxiranyl)-4-phenyl-1-((S)-1-phenyl-ethyl)-azetidin-2-one (917110-35-1) → (3S,4S)-3-((1S,2S)-2-Azido-1-hydroxy-butyl)-3-bromo-4-phenyl-1-((S)-1-phenyl-ethyl)-azetidin-2-one (917110-41-9)

Guidance literature:

With sodium azide; dimethylaluminum chloride; In hexane; toluene; at -78 - 20 ℃;

DOI:10.1021/jo0615652

Reference yield:

(1S',3R,4S)-3-bromo-3-but-1-enyl-4-phenyl-1-(1-phenylethyl)azetidin-2-one (847548-22-5) → (3S,4S)-3-((1S,2S)-2-Azido-1-hydroxy-butyl)-3-bromo-4-phenyl-1-((S)-1-phenyl-ethyl)-azetidin-2-one (917110-41-9)

Guidance literature:

Multi-step reaction with 2 steps

1: m-CPBA / CH₂Cl₂ / 20 °C

2: NaN₃; Me₂AlCl / toluene; hexane / -78 - 20 °C

With sodium azide; dimethylaluminum chloride; 3-chloro-benzenecarboperoxoic acid; In hexane; dichloromethane; toluene;

DOI:10.1021/jo0615652

Reference yield:

(3S,4S)-3-((1S,2S)-2-Azido-1-hydroxy-butyl)-3-bromo-4-phenyl-1-((S)-1-phenyl-ethyl)-azetidin-2-one (917110-41-9) → (2S,3R,6S)-2-((S)-1-Azido-propyl)-6-phenyl-5-((S)-1-phenyl-ethyl)-1-oxa-5-aza-spiro[2.3]hexan-4-one (917110-47-5)

Guidance literature:

With sodium hydride; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1021/jo0615652

upstream raw materials:

(3S,4S)-3-Bromo-3-((2S,3R)-3-ethyl-oxiranyl)-4-phenyl-1-((S)-1-phenyl-ethyl)-azetidin-2-one

(1S',3R,4S)-3-bromo-3-but-1-enyl-4-phenyl-1-(1-phenylethyl)azetidin-2-one

Downstream raw materials:

(2S,3R,6S)-2-((S)-1-Azido-propyl)-6-phenyl-5-((S)-1-phenyl-ethyl)-1-oxa-5-aza-spiro[2.3]hexan-4-one

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