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

Base Information

• Chemical Name: 4-nitrobenzyl (S)-4-((R)-1-tert-butyldimethylsilyloxyethyl)-(R)-1-((E)-3-nitro-2-propenyl)-3-oxo-1,2-diazetidine-2-acetate
• CAS No.: 174787-36-1
• Molecular Formula: C₂₂H₃₂N₄O₈Si
• Molecular Weight: 508.604
• Mol file: 174787-36-1.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about 4-nitrobenzyl (S)-4-((R)-1-tert-butyldimethylsilyloxyethyl)-(R)-1-((E)-3-nitro-2-propenyl)-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:

4-nitrobenzyl (S)-4-((R)-1-hydroxyethyl)-3-oxo-1,2-diazetidine-2-acetate (174787-26-9) → 4-nitrobenzyl (S)-4-((R)-1-tert-butyldimethylsilyloxyethyl)-(R)-1-((E)-3-nitro-2-propenyl)-3-oxo-1,2-diazetidine-2-acetate (174787-36-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / NaI, NaHCO₃ / dimethylformamide / 15 h / Ambient temperature

2: 91 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h / 0 °C

3: 1) NaI, N₂O₄, 2) NaOAc / 1) ether, THF, 5 deg C, 26 h; 2) ether, RT, 21 h

With 2,6-dimethylpyridine; sodium acetate; dinitrogen tetraoxide; sodium hydrogencarbonate; sodium iodide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.3987/COM-95-S32

Reference yield:

4-nitrobenzyl (S)-1-allyl-4-((R)-1-hydroxyethyl)-3-oxo-1,2-diazetidine-2-acetate (174787-28-1) → 4-nitrobenzyl (S)-4-((R)-1-tert-butyldimethylsilyloxyethyl)-(R)-1-((E)-3-nitro-2-propenyl)-3-oxo-1,2-diazetidine-2-acetate (174787-36-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h / 0 °C

2: 1) NaI, N₂O₄, 2) NaOAc / 1) ether, THF, 5 deg C, 26 h; 2) ether, RT, 21 h

With 2,6-dimethylpyridine; sodium acetate; dinitrogen tetraoxide; sodium iodide; In dichloromethane;

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)-4-((R)-1-tert-butyldimethylsilyloxyethyl)-(R)-1-((E)-3-nitro-2-propenyl)-3-oxo-1,2-diazetidine-2-acetate (174787-36-1)

Guidance literature:

Multi-step reaction with 4 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

3: 91 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h / 0 °C

4: 1) NaI, N₂O₄, 2) NaOAc / 1) ether, THF, 5 deg C, 26 h; 2) ether, RT, 21 h

With 2,6-dimethylpyridine; sodium acetate; dinitrogen tetraoxide; sodium hydrogencarbonate; toluene-4-sulfonic acid; sodium iodide; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.3987/COM-95-S32

upstream 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-hydroxyethyl)-3-oxo-1,2-diazetidine-2-acetate

4-nitrobenzyl (S)-1-allyl-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 (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

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