4-nitrobenzyl (S)-1-allyl-4-((R)-1-hydroxyethyl)-3-oxo-1,2-diazetidine-2-acetate

Base Information

• Chemical Name: 4-nitrobenzyl (S)-1-allyl-4-((R)-1-hydroxyethyl)-3-oxo-1,2-diazetidine-2-acetate
• CAS No.: 174787-28-1
• Molecular Formula: C₁₆H₁₉N₃O₆
• Molecular Weight: 349.343

Synonyms:4-nitrobenzyl (S)-1-allyl-4-((R)-1-hydroxyethyl)-3-oxo-1,2-diazetidine-2-acetate

Chemical Property of 4-nitrobenzyl (S)-1-allyl-4-((R)-1-hydroxyethyl)-3-oxo-1,2-diazetidine-2-acetate

Chemical Property:

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Technology Process of 4-nitrobenzyl (S)-1-allyl-4-((R)-1-hydroxyethyl)-3-oxo-1,2-diazetidine-2-acetate

There total 2 articles about 4-nitrobenzyl (S)-1-allyl-4-((R)-1-hydroxyethyl)-3-oxo-1,2-diazetidine-2-acetate 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: 94.0%

allyl bromide (106-95-6) + 4-nitrobenzyl (S)-4-((R)-1-hydroxyethyl)-3-oxo-1,2-diazetidine-2-acetate (174787-26-9) → 4-nitrobenzyl (S)-1-allyl-4-((R)-1-hydroxyethyl)-3-oxo-1,2-diazetidine-2-acetate (174787-28-1)

Guidance literature:

With sodium hydrogencarbonate; sodium iodide; In N,N-dimethyl-formamide; for 15h; Ambient temperature;

DOI:10.3987/COM-95-S32

Reference yield:

2,3-butanedione N-(4-nitrobenzyloxycarbonylmethyl)-N-((2R,3R)-2,3-epoxybutane)monohydrazone (174787-25-8) → 4-nitrobenzyl (S)-1-allyl-4-((R)-1-hydroxyethyl)-3-oxo-1,2-diazetidine-2-acetate (174787-28-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / p-TsOH*H₂O / acetonitrile / 0 deg C, 9.5 h; 5 deg C, 13 h

2: 94 percent / NaI, NaHCO₃ / dimethylformamide / 15 h / Ambient temperature

With sodium hydrogencarbonate; toluene-4-sulfonic acid; sodium iodide; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.3987/COM-95-S32

Reference yield: 91.0%

t-butyldimethylsiyl triflate (69739-34-0) + 4-nitrobenzyl (S)-1-allyl-4-((R)-1-hydroxyethyl)-3-oxo-1,2-diazetidine-2-acetate (174787-28-1) → 4-nitrobenzyl (S)-1-allyl-4-((R)-1-tert-butyldimethylsilyloxyethyl)-3-oxo-1,2-diazetidine-2-acetate (174787-32-7)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 0.333333h;

DOI:10.3987/COM-95-S32

upstream raw materials:

allyl bromide

4-nitrobenzyl (S)-4-((R)-1-hydroxyethyl)-3-oxo-1,2-diazetidine-2-acetate

2,3-butanedione N-(4-nitrobenzyloxycarbonylmethyl)-N-((2R,3R)-2,3-epoxybutane)monohydrazone

Downstream raw materials:

4-nitrobenzyl (S)-1-allyl-4-((R)-1-tert-butyldimethylsilyloxyethyl)-3-oxo-1,2-diazetidine-2-acetate

4-nitrobenzyl (S)-4-((R)-1-tert-butyldimethylsilyloxyethyl)-(R)-1-((E)-3-nitro-2-propenyl)-3-oxo-1,2-diazetidine-2-acetate

4-nitrobenzyl (2S,3S,5R,6S)-6-((R)-1-tert-butyldimethylsilyloxyethyl)-3-nitromethyl-7-oxo-1,5-diazabicyclo<3.2.0>heptane-2-carboxylate

4-nitrobenzyl (2S,3R,5R,6S)-6-((R)-1-tert-butyldimethylsilyloxyethyl)-3-((R)-nitro(phenylseleno)methyl)-7-oxo-1,5-diazabicyclo<3.2.0>heptane-2-carboxylate

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