(2R,3R)-2-[(3S,4R)-3-Azido-2-oxo-4-((E)-styryl)-azetidin-1-yl]-3-hydroxy-butyric acid 4-nitro-benzyl ester

Base Information

• Chemical Name: (2R,3R)-2-[(3S,4R)-3-Azido-2-oxo-4-((E)-styryl)-azetidin-1-yl]-3-hydroxy-butyric acid 4-nitro-benzyl ester
• CAS No.: 82730-04-9
• Molecular Formula: C₂₂H₂₁N₅O₆
• Molecular Weight: 451.439
• Mol file: 82730-04-9.mol

Synonyms:(2R,3R)-2-[(3S,4R)-3-Azido-2-oxo-4-((E)-styryl)-azetidin-1-yl]-3-hydroxy-butyric acid 4-nitro-benzyl ester

Chemical Property of (2R,3R)-2-[(3S,4R)-3-Azido-2-oxo-4-((E)-styryl)-azetidin-1-yl]-3-hydroxy-butyric acid 4-nitro-benzyl ester

Chemical Property:

Purity/Quality:

95%-98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-2-[(3S,4R)-3-Azido-2-oxo-4-((E)-styryl)-azetidin-1-yl]-3-hydroxy-butyric acid 4-nitro-benzyl ester

There total 2 articles about (2R,3R)-2-[(3S,4R)-3-Azido-2-oxo-4-((E)-styryl)-azetidin-1-yl]-3-hydroxy-butyric acid 4-nitro-benzyl ester 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:

p-nitrobenzyl-D-threonine (78963-69-6) → (2R,3R)-2-[(3S,4R)-3-Azido-2-oxo-4-((E)-styryl)-azetidin-1-yl]-3-hydroxy-butyric acid 4-nitro-benzyl ester (82730-04-9)

Guidance literature:

Multi-step reaction with 2 steps

1: CH₂Cl₂ / 1.) reflux, 3 min, 2.) RT, 1 h

2: triethylamine / CH₂Cl₂ / 12 h / Ambient temperature

With triethylamine; In dichloromethane;

DOI:10.1021/jo00142a015

Reference yield:

2-azidoacetyl chloride (30426-58-5) + (2R,3R)-3-Hydroxy-2-[(E)-3-phenyl-prop-2-en-(E)-ylideneamino]-butyric acid 4-nitro-benzyl ester (77821-71-7,78963-70-9,79082-32-9,91603-70-2,143061-83-0) → (2R,3R)-2-[(3S,4R)-3-Azido-2-oxo-4-((E)-styryl)-azetidin-1-yl]-3-hydroxy-butyric acid 4-nitro-benzyl ester (82730-04-9) + (2R,3R)-2-[(3R,4S)-3-Azido-2-oxo-4-((E)-styryl)-azetidin-1-yl]-3-hydroxy-butyric acid 4-nitro-benzyl ester (82730-05-0)

Guidance literature:

With triethylamine; In dichloromethane; for 12h; Yield given. Yields of byproduct given; Ambient temperature;

DOI:10.1021/jo00142a015

Reference yield: 37.0%

(2R,3R)-2-[(3S,4R)-3-Azido-2-oxo-4-((E)-styryl)-azetidin-1-yl]-3-hydroxy-butyric acid 4-nitro-benzyl ester (82730-04-9) → cis-3-azido-2-oxo-4-(2-phenylethenyl)-1-azetidine (78905-28-9,81767-89-7)

Guidance literature:

With jones reagent; In acetone;

DOI:10.1021/jo00142a015

upstream raw materials:

2-azidoacetyl chloride

(2R,3R)-3-Hydroxy-2-[(E)-3-phenyl-prop-2-en-(E)-ylideneamino]-butyric acid 4-nitro-benzyl ester

p-nitrobenzyl-D-threonine

Downstream raw materials:

cis-3-azido-2-oxo-4-(2-phenylethenyl)-1-azetidine

(2S,3S)-2-[(3S,4R)-3-Amino-2-oxo-4-((E)-styryl)-azetidin-1-yl]-3-hydroxy-butyric acid 4-nitro-benzyl ester

(3R,4S)-3-Amino-4-((E)-styryl)-azetidin-2-one

cis-1-<1-<<(p-nitrobenzyl)oxy>carbonyl>-2-hydroxypropyl>-3-(phenoxyacetamido)-4-styrylazetidin-2-one